My name is Melanie Stephens and I write a column for BiggerPockets Wealth Magazine on “Biggest Mistakes/Lessons Learned” in real estate.
I am looking for stories from BP members about that ONE deal or real estate opportunity that "got away.” Maybe it's a property you wish you never would have sold, or a real estate opportunity that presented itself but that you turned down, and now wish you hadn't.
In short, if you had a "do-over," you would have done things much differently - and, it taught you a big lesson!
If you have a story like this, I’d love to hear from you.
Please feel free to post here, or DM or email me with a few short details of your story and I'll get in touch with you if it looks like a good fit for the column.
melanie @ biggerpockets.com
Melanie, I have one:
Right after buying my first property (all this was before becoming an agent), I stumbled on a house for sale with an in-law suite and an extra lot. In my area, single family is very difficult to cash flow, so I was focused on multi-family. We offered $128,000 (way below asking) and it was valued probably around $190k at the time (it was very dated, but all cosmetic) and they took it. Turns out they were ready to get rid of the house....as we started to move forward I realized that even at that price after the rehab it wouldn't meet my cash flow targets so we passed on it. About 9 months later I see it up for sale for $330k. Someone bought it and flipped it and combined the units together as a single family. They payed $160k and sold for around $330k (without the extra lot) and I estimated they had $80k in rehab. I realized my mistake was being too focused on one strategy. I had a great deal and could have easily flipped it, etc. if I had focused on how to make money on the property and not just on one strategy.
I had an opportunity to purchase around 10 properties for 35-50k each. Every single one needed work. I saw every single one and took notes. I did not buy a single one. Taxes were around 6000 and rental income was around 1200/m so with the mortgage would not cash flow super high and did not seem to be a good investment. Fast forward 7 years those rentals would be rented for 1600 each massively changing the ROI and cash flow and each are worth somewhere around 150,000. I wish I bought every single one.
Oh man, just had one the other day. I bought a 4-plex in 2017 in Ann Arbor, which is an incredibly stable area that provides awesome appreciation. Michigan's version of Denver. It was two duplexes on one lot. The place was a bit run down and the units needed some work, but the whole area around it was still developing. Even in its run-down state it was bringing in about $4,400/month. I could've fixed it up and bumped the rents to $6,000/month. That's what my gut told me. Unfortunately, I was afraid of the $000s associated with the renovation and thought the market would take a downturn after a 10 year upswing, so I tried to time the market.
I contacted 5-10 local multi-family buyers and did some off-market showings. Everyone told me I was asking too much, except for one young local broker who bought the property (with an FHA loan if I recall correctly) and house-hacked it. I usually take it as a good sign when 90% of buyers say I'm asking too much but one is willing to pay it. I bought for around $415k and sold 7 months later for $548k. Paid short term capital gains on all of it.
The buyer did some cosmetic changes and held for a little over two years. Fast forward to early 2021, and I see it listed again for $695k. "No way he gets that" I say. It sells it for just over $680k. Total gut punch. I could've held it, sold a few years later for $130k+ more and done a 1031 into something $1mm+.
If it cash flows well, keep it...especially if it's in a solid area. Don't try to time the market.
The one I have in escrow right now! It's most likely going to be canceled because the seller needs to expunge a wild deed off title. She knew about the deed but thought it was settled, but title needs it expunged to convey clean title and insurance. The seller disagrees (even though she's not a title expert), and refuses to any extensions. She just wants us to close. We keep explaining that we are ready to close, we just need her to follow the contract which states "seller shall make reasonable efforts to cure title defects" otherwise she cannot convey title. It's so backwards.. she's making it seem like it's our fault, and she might actually think it is (depending on whether she is listening to everything I've explained to her or not). Anyway, she's pretty much told us she's going to cancel.
Another one was a condo a friend of mine referred me to. Seller moved to the mainland after her husband passed and was going to let the bank take it. She owed 200k, it needed 50k rehab, and ARV was 450k. Perfect numbers. That is so hard to find in a place like Maui! Well my friend sent and email intro saying I wanted to buy it, but I never followed up. He later heard that she doesn't not have access to her email but was interested in selling it for what she owed, so I got on it right away then, got her number and when I called her she said she had just accepted another offer from another flipper the day before. He paid 200k and sold it for 440k 2 months later. I blew it.
both properties I owned in Palo Alto Ca one I bought in 83 for 185k todays value probably 2.5 mil to 3 mil.
the other I paid 500k for in 87 today easy 4 mil.. did not need to sell them at the time. they were single family but they would have been negative cash flow by 300 a month on a one and 500 on the other.. LOL
All right, guys, this is a longish story, but the way it went down was complicated and I swear I'm not making anything up. It was early in the game for me. I found a property that matched my criteria at the time as a tax foreclosure. Was determined to buy it at the county tax auction. I ended up in a bidding war against, of all people, an elderly man dressed like an extra in Fiddler on the Roof. An unusual sight at the tax auction, but not really in Pittsburgh's Squirrel Hill neighborhood. We went up to my limit, and I stopped bidding. I was disappointed. It was a good house. I had actually managed to get a look inside as well to confirm that it was in pretty good shape.
Now, the way it works in Allegheny County, you pay a 10% deposit on the winning bid up front at the auction and if you don't pay the 90% by the end of the week, your deposit goes into the sheriff's pocket and the property goes up for auction again next month. I didn't see anything the next month I wanted. I decided not to go. And I didn't check if the guy had paid the rest of his 90%. The bid was $35K. Who throws away $3500 just to look at the property? And I knew from experience the property was in good shape inside. No reason not to pay the rest.
The guy didn't pay his 90%. One of the main bidders, a wholesaler, picked it up for $10.5K at the second auction. When I found out...oh, I was upset. But I called the wholesaler, agreed to pay him $28K cash for it as soon as we were out of the month-long probationary period we have here in Allegheny County. While the property was sold free-and-clear at the auction, I started digging into the title down at City-County Building, in the actual deed books. I found some fun stuff there.
So back in the early aughts we had a guy here, call him Dov, who took advantage of Bush-era deregulation to run the following scheme. He managed to come to terms with a loan officer in a bank. Then, Dov rounded up subprime buyers in the ghetto who did at least have a steady job. He promised them a house with "no money down" if they just kept mum and signed whatever paperwork was put in front of them. Dov took them to the bank where his accomplice worked, opened up a bank account in their names, deposited $25K or thereabouts in it. The subprime buyer, with their sizeable balance, now qualified for a loan on a low-cost house. Dov provided the low-cost houses, which he bought dirt-cheap as mortgage foreclosures. He sold them to his newly-minted straw buyers at retail price. The small down payment came out of the money that was in their bank accounts (Dov would withdraw the money a month later). Hey presto, now the buyer had a house with no money down!
But Dov's buyers were, of course, really subprime buyers. Almost all failed to make regular mortgage payments. The bank foreclosed on the houses, put them up for auction. Dov would buy THE SAME HOUSES again, and he could get away with using them in the same scheme a second, third, fourth time. The money rolled in until the feds started sniffing around. But by now, Dov had enough money to abandon Scam #1 and start Scam #2, a classic property management Ponzi scheme.
Dov flew to Israel, booked seminars a few cheap hotel conference rooms, and convinced investors there that he could make mad money on property in Pittsburgh. The buyers would put up the money, he would buy the house, renovate it, put tenants in it, manage the property, send the money back to Israel.
We all know exactly how this works thanks to Clayton Morris/Burt Whalen and the Oceanpointe debacle, and @James Wise 's work in exposing that massive real estate Ponzi scheme in Indianapolis and elsewhere. Dov paid off his initial investors with proceeds from additional investors. The scheme got bigger and bigger. The cracks started to show. Some investors flew in from Israel to find their properties were abandoned and unlivable.
Eventually, Dov got arrested on a federal warrant and the judge took away his passport. Dov still tried to flee on bond. They caught him in Florida trying to get an Israeli passport. Dov's in the federal slam now, doing his bit.
But here's me in the City-County building, finding that "my" property has been foreclosed on again and again by banks, and then bought sold again and again by entitles with names like "Admiral Capital, LLC" and "Realty Choice, LLC." I go to the computer and find the news stories. Judging from the dates on the deeds, "my" property was one of the first properties to be put into Scam #1 and one of the last property to be sold to Israeli investors in Scam #2. The thing that blew the lid off Scam #2 for me was finding that Realty Choice's "office" was actually an MMA gym. I'm not saying all fighters are sketchy but, well, you watched Kingdom.
I bring my concerns to the wholesaler who bought the place. He assures me everything is fine. He knows the system. Don't worry.
And then the shoe drops. The mark in Israel finally makes an appearance, gets a judge to issue a hold on the sale. The wholesaler tells me it's going to be fine, don't worry. I pull out and get out of that mess. And let me make no bones about it, the wholesaler was damned decent about it, actually. I'd buy from him again in a heartbeat.
In the end, the wholesaler ended up holding the property for over a year until the hapless Israeli investor was sent packing by the judge and the property was finally sold to someone else for $28K.
To this day, I wonder what was hidden in that house that was worth $3500 for the Fiddler to look at (and possibly move out). Was it a coincidence? Was he linked to Dov? To the Israeli owner? I'll never know.
I was offered a portfolio of 16 townhouses in NOVA for about 65k a pop. The properties in question are in a hard hit area, that everyone says will gentrify, but it never does after two decades of people saying that. I had just wrapped up another deal, so I passed because I was getting nicer deals for about the same price in other areas.. This was maybe 4 or 5 years ago. Between that time and now, the city bulldozed some buildings, built two parks, then tossed in a 4 lane highway, and 3 new apartment complexes got build next door, along with a new housing development and a few motels... They sell for 185k a pop all day long, and rent for $1,650 faster than you can list them.
Back in '87 I had an offer in on a large 2 acre lakefront property with a large old burned out home on the road. Went in & got contingent at $225k but being burned out I couldn't get conventional financing (18% at the time) or talk the 4 partners (aka their wives) I had on several other properties to invest so I reluctantly let it go. The old home was eventually completely rehabbed & the land was then subdivided into a T lot. Allowing 2 homes to be built on the waters edge. The restored home on the road sold some years later for $750k & I bet today the two on the water are now worth over $2mill each.
I think we all have these stories. I wanted to just put in the note to not kick yourself too much over the deal that got away, as hopefully, you are still out looking for the next deal or thinking about how you could make one even if you don't think you have the funding or a way you could manage another deal right now. As if you are always looking and you come across a great deal you may be able to find a way to better adapt your business to do more investments, find different ways to fund them, or sell deals to other investors that may build relationships down the road for joint ventures that will benefit you both while putting some money in your pocket and helping that investor out!
While growing up we had a crazy neighbor who lived across the street from us. He was a concrete contractor, who built the house himself over a couple of years. He was likely a drug addict and would be doing work on his house at all hours of the night. I would be fascinated to know what his actual medical diagnosis might be because he would work his butt off and had some great ideas in design areas. It was a really well designed and looking house. Anywho, during my college years, he got into some legal trouble, the house went pretty much abandoned for 3-4 years. My Dad, a union carpenter lived right across the street and I kept telling him to just buy it(zero real estate background or investor ambition in my family). He thought I was crazy. A couple years went by and I was focused on school and starting a career. It eventually sold for $28,000 to a flipper I've gotten to know who put $26,000 into it and sold it 6 months later for for $155,000. This is in a market with less than average appreciation. A childhood friend of mine lives in it now and just refinanced with appraisal of $255,000.
There was a package of 21 houses all built in the late 90s, rented and in mostly good shape near downtown Kansas City, KS (which admittedly isn't much of a downtown even compared to KCMO). The property were each worth about $125,000 fixed up in my estimation. We came in over asking at $1,925,000. It sold for $1,975,000. We should have just gone a bit over $2 million. Ugh.
Mine isn't a specific deal but actually a way of operating to complete the deal. Let me start off by saying that I've been researching real estate investing since I was a teenager and pursued construction to learn how to renovate the houses myself. Due to my experience I felt it be necessary that I do the work myself to keep down on construction cost. So our(My wife and I) project we successfully finished a beautiful flip but it took us 6 months longer than we expected. So I decided then on the next deal I would outsource everything and do zero physical work on my own so I could scale quicker and do more projects. I will jump out of the plane and install my parachute on the way down while my wife will watch hours of you tube on how to install her parachute before she even considers jumping. So at the time I started running a renovation company and started doing projects for other investors as well. Things were going pretty well. Tons of work doing a personal flip plus 4 other projects who could complain. Well next thing you know the pandemic hits and I run into a few issues is manpower and now instead of spending the time to find different crews I get this wonderful idea to just do it myself because I can! So I decided to work 7 days a week to play catch up to finish my flip and complete out all my client projects. During this time I was not focused on finding new subs, or more deals, or more money, or more strategic partners. All I was doing was damage control. I was in the day to day of my business and wasn't focused at all on growth and development. I fell down the rabbit hole and couldn't pull myself out. Now that I finally pulled myself out deals are harder to come by due to the market and now I have to focus on re-building what I was already halfway there a year ago. Not that big of a deal since in the grand scheme of things I am net positive but I definitely lost money on some client projects. Lesson learned here, Stick to the goal. Don't do things just because you can. I did this and it caused me to regress and go backwards instead of continuing to build and move forward. I am in a much better place now but I did lose a great deal of time personally renovating other clients investments instead of focusing on my own and progressing forward in my goals.
Make a plan and stick to the plan. Don't be lured into a quick $10,000. Its just a bathroom. Nothing is quick and nothing is "just a..." in this industry.
I purchased a SFH for $130K. I held onto it for about 8 years waiting for it to appreciate as it had seasonal water. I knew eventually it would be a year round house. I sold it for $125k, as I got tired of waiting for the water. Less than 2 years later it was year round and my buyer sold it for $325K.
- Was offered a 3bed 2 bath house in "Hornsby Bend"... whoever heard of such a place? For 175,000. 10% down and owner would finance the rest at 6% amortized over 20 years, no balloon. The place needed work and foundation needed leveling but it was leased and the tenant had been there for 10 years and wanted to stay. Then Tesla moved in across the street in East Austin and I feel sick basically every time I sell another house for 300k+ on his street... hah
I had just moved to St Pete, determined to find a small multi to hack. I have an awesome agent who is also an investor, so she found me lots of good properties to look at, but they kept escaping me. I had my budget set at $400k. So that's when I found two.
The first was a quad, pre-market, still had some work going on, and they were planning to put it on the market in a few weeks at $450k. I told my agent to see what they thought about $400k, and she reported back that they were warm to the idea. But that place wasn't a good fit for me, as a personal residence, and I still needed a place to live.
Around the same time, we found a duplex that was a good candidate for my house hack, so I put an offer on it and called a friend to partner on the quad. I sent him all my numbers, including the BP calculator, and he was in. He'd bring the down payment, and we'd split it 50/50. It was a cash cow!
An important detail here is that my W2 takes me out of the country for months at a time, and I had a departure date looming. I actually had a POA for my sister to close on my house hack for me, because I thought I'd be gone by the closing date. Feeling the time crunch, I told my partner that since it would be my first deal with a partner, as well as his, I wasn't comfortable risking his money when neither of us could be on site for closing, final make-ready, etc. He thanked me for being up-front about that.
Then the world shut down. I was stuck in the States, unable to travel to my worksite for nearly 3 more months. I could have closed both, done touch ups that the 4-plex needed after the "renovation" the seller was botching, gotten it filled and been collecting a big pile of money every month.
Melanie, the deal that got away is one that I still think about. It was a raw land deal that involved buying the land, creating the infrastructure, drainage, utilities & subdividing the land - then building custom homes on the lots (development) for my family which they would then eventually sell off and profit from.
My family had found a 15 acre tract of land listed for sale at $500,000 ($33,333 per acre) in a very fast growing area of Texas. I knew this land was a deal when I found it, and I visited the property and it had never been visited by the seller as they were out of state.
My plans were to subdivide the land into 5 tracts of 3 acre lots, install an access road to each lot, and have a middle pond / drainage area with a fountain.
While completing my due diligence (this took months) I was finally ready to move forward with the deal. I had figured I needed to put in another $150-200K in improvements to the land before we could build out homes.
All in, I would be around $700,000 for developed turn key lots, which in turn would be worth $2,250,000 at completion ($150K acre). Homes would be custom built, and would build out for around $150 / ft. putting the value of the lot prices with homes in the range of $700-850K.
Looking at it from an investment deal, we stood to make potentially over $1M after the debt was paid, costs were covered, etc.
It took me months to finalize my costs, and line up financing with a local bank who would finance the initial land, and then refinance the individual lots to the end buyers.
I went to move forward on the deal, and the day we reached out to the other agent to proceed we were notified a church bought the property - and that was it for my deal.
Although this deal cost me nothing but a few months of due diligence, I learned that you need to move forward if your gut feeling tells you so. Someone else is looking at that deal. Don't wait.
Great story idea... looking forward to the article. Here's my story.
My wife and I work as a team when it comes to our properties. We've been doing long term rent/hold for a while and were looking to jump in the short term rental space. We came across a property in Harrison West. It was a Single Family home with Accessory Dwelling Unit converted into 2 condos. We were looking the smaller unit (previously ADU). 1 bed, 1 bath, nice kitchen, new mechanicals throughout, great outdoor seating area and a garage.... and did I say Harrison West. The price point was $206K.
The problem on the deal was the condo decs & bylaws did not allow for short term rental. However, the Seller of the condo, owned both units and said he was willing to amend. With it being our first attempt of getting into the Airbnb space, we acted like a newbie investor and started finding reasons to not do the deal and walked away.
We eventually did buy our first Airbnb property and now know that the condo we passed on would've been an absolute gold mine for Airbnb. Still hurts today.
That would’ve been a nice Airbnb!
Every investor I know who’s active in this market has a story similar to that. Hindsight 20/20!
Hope you and Jenna are killing it on your Airbnb’s!
The one that we had get away, our very first attempt could have and should have been a grand slam but unfortunately was a swing and a miss. My first attempt to break into Commercial Multifamily was on a parcel containing 3 4 unit buildings, the buildings were in complete disrepair and had two of the buildings appeared to be vacant for some time, the third looked like someone was living there. I made several attempts to contact the owners of the properties for 4 or 5 months with no luck. I had even parked outside when I had time in hopes of catching the owners, I would swing by at different hours and days, tried to catch them putting out the trash everything. I knew the owners were elderly and could not find an email, or cell phone number for them and got no answer or machine on their land line.
I talked to the neighbors, local real estate professionals and no luck. I was working as an agent for a local broker at the time and the closest I had come was she knew of the owner but hadn’t seen or heard from him in years. From what I was told he was less then agreeable and had run a fowl of the city, hence the vacancy. He also owned a building across the street, also vacant with a big sign he had put up to spite the city. I finally managed to catch the mail man one day and I engaged him, he informed me the owner had passed back in September, it was now February, turns out I had missed him by just about a month when I had begun trying to track it down. I gave the Postman my card and he said he would pass it to the family if he saw them….. Nothing heard
While trying to track down the owners I had meetings with city officials and ultimately sat with the planning department to see what the options were regarding the property. They had been vacant now for so long that the zoning had changed and they were not grandfathered in. Due to street frontage and parking requirements in the city they would not be able to be used as quads. They would need to be torn down or converted into duplexes at best, after 3 hours with planning trying to hammer out the possibilities that’s what I walked away with, but at least I had the city on my side.
I went back through and skipped the owners again and by chance and a long rabbit hole I managed to locate the daughter (who had been estranged) she was not easy to find and I really only happened upon her by sheer luck. I cold called her and she was on the fence about selling the property, she was contemplating doing the work herself but said she would entertain an offer.
My First MF offer, after learning what I had my valuation on the property had dropped significantly and my first offer was at land value for the 3 quads, I also offered to purchase the ne across the street at land value as well just to get it out of her hair. When I had spoken to the city there was no options aside from tearing down the other building, it is an 8 unit 1BR, 1BA sitting sideways on 1 lot with no off street parking, it also had a partial roof collapse. The parcel would only support a single family unit and that’s all the city would go for.
The owner scoffed, and was quite offended, I got an earful about it. There would be no counter from her, and no further contact. I would try and call every couple weeks, and email when I thought about it but I just kind of gave up on it, licked my wounds and carried on.
A year later and as luck would have it I was heading out to look at an eight unit building on the corner of the same street, when I arrived I looked over, at what we had nicknamed Arthurs place (owners name), and the 3 quads were gone. Just a grass field remained and a mound of dirt, I could not believe my eyes, after I toured the 8 unit (that I ultimately purchased) I fired up my laptop and went to the city’s website. She had sold Arthurs place for 5k more than we had offered a year prior just a month prior $300,000.00. The developer has since torn down Arthurs place and split the lots, with plans of erecting 3, 3 story Duplexes, they will sell for somewhere in the mid $500’s each.
The lesson we learned that day was persistence and follow through, we had done everything we could to secure that deal, all the research, the planning and evaluating we were ready to go. The seller was not, and we didn’t follow up and follow through that deal was lost because of our in action, and nothing more. It wasn’t all bad though I learned a ton about the market during the pursuit of Arthur’s place, an education that I may not have gotten otherwise. Arthurs place is what propelled me into action, and forced me to get uncomfortable and even without landing that deal I have earned much from it.
Be smart and talk to your neighbors. After purchasing my first property (flip to rental) and aiming for deal number 2 I found out my old neighbors were selling. They owed $90K (great deal for the neighborhood) and were in pre-foreclosure. It ended up selling for $120K. Had I been friendly, helpful, and asking the right questions I could have purchased the house off market. It would have been a great investment and got me into the game 5 YEARS EARLIER.
Talk to your neighbors.
@Melanie Stephens Upon reading your topic and reflecting back on deals (plural) that I had in my hands but let it go due to bad judgment or miscalculations, it became too overwhelming for me and suddenly I started to have feelings of disappointment, upset, and bitterness ... so I immediately had to stop thinking about those lost deals and go out for a run! 😭 lol
So I got my first wholesale deal in the works. Did everything I needed to do and got the property under contract. I got a good price that worked for everyone. Seller would get 305k I'd get 15k and the buyer would make well over 100k after flipping. I had a few different people come check it out until I finally got the buyer. I did all my rehab numbers correctly and got a buyer agreed. (I'll mention now that the seller was a senior and had a lot of mentally draining things going on, her daughter and nephew recently passed away) and she just wasn't to mentally stable but going on we get to the last contract and the buyer is all ready. I guess will covid going on they bought a property or two that the seller sold to them but wouldn't move out and they wouldn't take the property not vacant. Problem is the seller wanted to use the money to buy a townhouse. I tried to work out something because I understand both sides. I trusted her and I knew she wouldn't try anything like that but they didn't know her. They offered to pay her some money upfront and the rest after closing vacant. None of that worked out and we were at the end date the contract with the seller and she didn't want to keep going because of everything else she had going on. So I had to drop the deal. I was disappointed but it motivated me even more because of how much I accomplished on my own in a just a few months of getting into real estate. Its the one that got a way but the one that started it all.
There's a house in my neighborhood I walk my dog by more days than not. It listed on the MLS—not even off market!—last summer for $125,000. The average in my area for a 3/2 was between $175,000 and $200,000. I wanted the house badly and asked my real estate agent to get us a showing.
He got us out that same morning on his way to his kid’s soccer game. At the time I had one rental property, and though I’d studied hard, and learned as much as I could, I still leaned on my agent heavily. We walked through, and when I asked his opinion, he indicated it was too much work for his investment preference. Nonetheless, I asked him to put in an offer for $125,000 cash, closing at whatever pace the seller wanted.
Surprise! I didn't win. But…four months later I saw on Zillow that it sold for $126,000. This would have been a live-in BRRRR for my family, and the kicker is, the basement had a nice 4th bedroom framed in with an egress window, giving us extra space for our family of five. I’m angry at myself for not doing the mental math, and angry at my agent for missing the dang bedroom, and angry at myself for leaning on my agent because I was too afraid to assert myself.
Now, when I walk past that rehabbed house, which sold again this February for $235,000, my heart still races. I think my dog even senses how upset I am at myself for letting that house get away because he always barks when we’re going past that driveway.
Free eBook from BiggerPockets!
Join BiggerPockets and get The Ultimate Beginner's Guide to Real Estate Investing for FREE - read by more than 100,000 people - AND get exclusive real estate investing tips, tricks and techniques delivered straight to your inbox twice weekly!
- Actionable advice for getting started,
- Discover the 10 Most Lucrative Real Estate Niches,
- Learn how to get started with or without money,
- Explore Real-Life Strategies for Building Wealth,
- And a LOT more.
Sign up below to download the eBook for FREE today!
We hate spam just as much as you