For me the bad mistakes cost the most money. And I am a contractor So I am going to go with a home we remodeled and the plumber rerouted one of the drains and never tied it into the main under the basement slab . So naturally we finished the basement. Drywall, paint , trim flooring, kitchenette, bar the whole deal! Then we ran through our normal QC to find a major back up. Of course the connection that needed to be made was located under our newly tiled floor. About 4k later and 2 weeks of delay you would never know..

@Dallas Kidd YIKES!!! 

Biggest mistake so far... getting a deal under contract... my broker secured financing but closing the deal depended on successfully refinancing one of my properties. The broker couldn't close the refi deal and instead tried to get me into an alternate loan (ARM for 5yrs). Needless to say I lost the deal because I was depending on the broker to do what is in his expertise to do.... lessons here...know the underwriting process enough to know what is possible, build a relationship with an honest broker who is transparent upfront and have a back up broker/someone versed in financing to run the scenario before locking up a contract....

I forgot to check a property for aluminum wiring prior to going under contract. I was so caught up in the home's rehab potential that I completely forgot to use that screwdriver I was carrying to check. It ended up costing me an additional $3100 to remediate, won't make that mistake again.

Trying to create shortcuts by believing something will not a problem, trusting the seller, or trying to do less work or save a few pennies. The biggest problem I ever ran into was one of my first ten houses I flip, it maybe have been project 7 or 8, and I took the seller at their word with an addition that they had stuck on the house that they had done everything right, by the book, and more importantly up to code. I trusted the seller, and never bothered to investigate it thoroughly or due my own due diligence on the matter. That house became never ending battle and fight costing me way more money, and way more time, and to this day still has my personal record for longest flip done at almost a full year. I get angry at myself just thinking about it, but it taught me that the extra work is well worth it to look into and there are not any corners to cut to when it comes to knowing the project you are taking on. 

@Dallas Kidd I bought a house to use as a short term vacation rental only to find out city has a 90 day minimum. Ugh. Luckily it doesn't cost much to keep.

They say confession is good for the soul so here goes.....my CPA suggested that I could qualify as a 'real estate professional' and take advantage of the very favorable IRS tax treatment which accrue to investors with that designation. The rules for qualification as an R.E. professional are complex and I trusted my CPA so I told him to go ahead with it. He filed 3 amended returns and I rec'd 2 big refund checks. Instead of that 3rd refund check though I rec'd a letter from the IRS challenging my CPA's understanding of the IRS rules re R.E. professional status. Long story short is that I had to hire a tax attorney for $4k and I have to pay back those 2 refunds with interest but fortunately no penalties. Moral of the story is, if it sounds too good to be true.....well you know the rest. 

@Dallas Kidd My biggest regrets over improving on buy and hold rentals and taking my sweet time getting g these rentals rent ready. My biggest mistake would be not buying more post 2008! Not using OPM. I was always reluctant to take anyone's money. So next time I wont think twice. You live and learn.

@Dallas Kidd I installed floating vinyl tile over padding, not realizing the flooring should not go over padding. sadly, did not realize until after I put it in 4 houses. as of now, only 1 house needs replaced, but I am sure others to follow.

@Wayne Bodley in what city?

@Dallas Kidd . I usually tell people so far I haven’t made a huge mistake such as getting ripped off by a contractor or buying in just an awful area. That being said I’ve made a lot of smaller mistakes. Here are some: paying too many lender fees on my first purchase. 2. Paying a lawyer almost 1000 for a llc I could have done myself of 99 dollars.

I still have an IRA with a private financial planner who's obviously ripping me off on fees every day.

I'm still neck deep in a rehab a year after I had originally planned to have it done. Thankfully, it hasn't cost me quite that much in holding costs.

But my biggest real estate mistake of all was the six years between selling my last flip and buying my first rental property. I was stupid and shortsighted and wanted to save the world instead of "filling my own cup first." I simply did not understand much about how real philanthropy works in this world.

Not what i would call a mistake but more of a shoulda woulda storey.

IE sold the first house i bought in Milpitas for 79k  ( worth 800k today)  sell the first house I bought in Palo Alto for 185k

( worth 2 mil plus today) Sold the house I owned in the napa valley that i paid 410k for ( value today 1.7).  

But they would not cash flow  LOL.. but I still made almost 500k tax free on palo alto and napa when i sold them as my primary residence each.. so not all bad.. 

other than that was not selling all the real estate i owned in 06.. again who was to thunk it.. world was going to come to a real estate end in 08 to 2010.. bout killed me..

Listening to a former client whom recommended a company in Nevada to set up an LLC for me. Then taking that LLC and forming in California. The scenario isn't bad, what's bad is that I ended up $1,500 out of pocket when I could have filed everything myself for about $200. At the time, it was all new information to me and I assumed these companies would be legit to assist. Nothing further from the truth, this company offers "compliance coaches" who are more like salespersons because all they do it try to lure you into buying more services from them that are not even necessary or it's something you could do yourself. It was funny to experience their changes in their approach once they realized I had figured out everything related to this field. Same cases for Trademarks. Attorneys will charge arms and legs, but you can do it yourself successfully for about $300.

I don't really look at them as mistakes, but rather hard lessons. And fortunately I have a lot of them under my belt pretty early on, better to get them out of the way now. 

In my situation, they were inevitable. The perfect deal was never going to be there, I had to make the best of the opportunities presented to me at any given time. Sometimes I handled them good, other times not so much.  

The list is just too long, but I have learned a lot in a short period of time.

@Dallas Kidd my biggest mistake was not to check IDs of the tenants after Ive purchased a rented house. One of my tenants subleased his room to a criminal. I did not loose any money, but Ive lost my sleep after the guy thretened me and my family. After this event I tell all my tenants that I dont allow sublease before I check the records. Oh gosh, these memories are unpleasant :(

Not buying more property from 2008-2013.

Originally posted by @Jim K. :

I still have an IRA with a private financial planner who's obviously ripping me off on fees every day.

I'm still neck deep in a rehab a year after I had originally planned to have it done. Thankfully, it hasn't cost me quite that much in holding costs.

But my biggest real estate mistake of all was the six years between selling my last flip and buying my first rental property. I was stupid and shortsighted and wanted to save the world instead of "filling my own cup first." I simply did not understand much about how real philanthropy works in this world.

Could you please elaborate on this?

@John Boychuk

What does that mean? Do you want a hard-hitting expose on how my CFP is taking me for a ride? Details on my neverending rehab? L'histoire de ma vie? Or all three? How ya like buyin' Kindles?

@Dallas Kidd Mine was not understanding seasoning requirements on my first buy and hold rental. I purchased it with cash thinking I'd be able to refinance it once all the upgrades were done and pull my cash out quickly. Found out if it is still under 6 months after purchase the only amount which can be refinance is the original purchase price, not the new appreciated value. Lucky had given myself a back-up plan and it cash flowed well though much more aware now.

@Dallas Kidd Bought 18 acres and paid to have the property surveyed, twice. Second time was to subdivide into a minor subdivision. First time was to show no encroachment (pond) to the bank lending me the money to purchase. Hindsight and I would have had the subdivision created at the first survey.

Took my wife with me to look at a duplex in a not so great neighborhood. It wasn't a really bad area but she wasn't comfortable and told me to "turn the truck around, don't make eye contact and get the --ll out of here" It was a property that I could have assumed a VA loan with no money out of pocket except a couple thousand in rehab. Now 20 years later it would be paid for and cash flowing $1200-1500 a month. Since then I've had better success in letting her look at the properties after I've rehabbed them and not before.

@Beth Turner I’m an accredited investor who’s also been buying in KS MO. I purchased 26 units in last 9 months near Westport and I’m under contract for 28 more. Let’s talk. Jason #streetcar extension $

Biggest mistake? Sitting on my hands.

@Mike Dymski . Mic drop

@Jason Graves you had me at streetcar... let's talk fast cars.