Woulda Shoulda Coulda whats some of your best ones in RE

13 Replies

Mine was selling anything I owed in the SF Bay ARea... And there was a developer in San Jose named McQuen who built hundreds of 4 plex's that were converted to condos. they were the style were two are ground units 2 upstairs and 4 car parking underneath in the rear. they were selling for 5900.00 a door in the late 70's and there were loan products were you could buy them with 500.00 down and payments were about 250 a month.. but rent was only 200... So of course who could afford 50 a month in negative cash flow.

Those units today sell right at 300k each and rent for 1200 to 1500 a month... I had one client that owned 80 of them... I shoulda and coulda   bought half a dozen

@Jay Hinrichs  , I'm trying to learn from more experienced investors like you, and after my 4th deal, have still not sold anything! I don't plan on it either!


In 2011 I believe, while I was scouring Lake Merritt and West Oakland for a big 4plex to buy, and couldn't get into contract on anything w/ an FHA loan, I came across an off-market 4plex close to Lake Merritt that hadn't been occupied in years, and was stripped down to the studs inside.

I didn't know much about construction costs, didn't know much about 203k loans, and didn't have a network of awesome investors like I do now, to see the project through. It looked like too much risk for what I knew at the time, and maybe it was. If I would have got it done at a reasonable cost, I'd probably be up about $300-500K on the property, $8k/mo in rents, and may have quit my job already.


Fast forward a few years now, and that's exactly the deal I'm looking to come back around and do now - a 203k on a big 4plex near Lake Merritt or another desirable area - possibly West Oakland.

I would kill to be able to find that exact same deal today, even at another $200K.


@J. Martin  

  I thought this subject would get more play then this.. But I think its probably a west coast and upper east coast sentiment were properties have gone nuts.. Its not Hey I could have bought that house in Memphis for 50k and its worth 60k 12 years later.. or I bought this house in Detroit 7 years ago for 100k and its worth 2k today...

Just being fatecous but I think since no reponses its a deep west coast thread and I probably should have entitle it.. Hey were you in the Bay Area in 1970 and 80 like me and what are your most shoulda woulda coulda stories..

I was still really new to REI. I had never even closed on a single house yet. I didn't trust my gut. I found a MF 100+ unit for 10k a door. It was in a C+ B- area and had some minor rehab. Instead of buying it. I told a business guru friend and only did a passive investment.

It is now worth 45k a door. From 40 to 95% occupied. Need I say more!

well but it wasn't even my 10%. A preferred investor has to have 1 million in assets. I didn't have that so my father did it.

I could have had it out right.

coulda woulda shoulda bought the fertilizer plant a friend offered to sell to me for 45k in 09 that just sold for over 300k with no improvements just some other lucky guy sat on it until the economy came back didn't even use the buildings just left them empty and paid his taxes....

Jay, I suspect you are right about fly over state investors not having as big regrets on not buying since there generally hasn't been 5x or 10x appreciation.  Like Michael, though, I have seen some Texas apartments double in just the past three years. 

Woulda Shoulda Coulda allocated a bigger portion of my investments to cash flowing real estate when I first started out (2010).

I was offered a multi family a month ago and turned it down. Person who bought it to me flipped it himself and made a mil :-).

Bought a house in Phoenix in 2010. Had so many hassles with dishonest management we stopped buying there. Sold it 2 years later and tripled our money. Shoulda bought 50 houses there :-)

Circa 2011  I should have bought every home I could have bought in Henry county GA.

and every lot that was 3k and under.

Back when I was about 19 or 20, I was living the good life with a very well paying full time job, fresh out of a 2 year tech school and still living with mom and dad - no wife, no kids, no mortgage, no medical bills, none of the burdens or blessings of life I have today.  I graduated high school in 2007, started tech school in that same summer of 2007, accepted the full time job in 2008 and due to the condensed course schedule, graduated in the winter of '08 and was promoted.  So in the course of less than a year, I went from making practically nothing to what my "poor" college friends called "baller" status.  Meanwhile, my wife - then girlfriend - was still a junior in high school...so, even though I had often considered myself to be really frugal, I just wasn't at a point in my life where financial planning was a priority and was sort of thrust into an income that I quite exaggeratedly didn't think required me to be so frugal anymore.  Side note:  It's probably the same mindset people have living pay check to pay check and winning a million dollar lottery - it isn't a bottomless figure.  Anyways, I'm getting off track.

Instead of investing in real estate (or anything at all), I decided I just had to have this 2001 Ford Mustang Cobra.  I had always been a Mustang fan and owner since getting my license, so I figured at that point, it was as good a time as any to build my dream my car.  2 years later, several thousands of dollars in performance parts, a blown engine, a rebuilt engine, blah blah blah, I had a 600 or so horsepower convertible performance car and absolutely zilch in savings or investments.

Around that same time, circa 2008, as I'm sure many of us can recall, the financial crisis was in full effect.  Despite the fact that it was probably the greatest time in my life to dump loads and loads of cash into cheap, undervalued stocks, instead I kept pouring more and more money into a car and performance parts which were more or less worthless from a financial perspective when you sell a car - unless you can find an absolute buyer.  Of course, hindsight is 20/20, so I mean, of course I couldn't have predicted that Ford stock would go from less than a dollar at one point to over $18 a share early in 2011 - it sits at $13.79 today.  I often consider if instead of dumping $1000 here or a $1000 there into some pistons, supercharger, exhaust, etc and put it in a S&P500 tracking mutual fund how my life - financial or otherwise - might have been different.

But then, in that same breath, I often think of how perhaps everything happened exactly as it is supposed to in my life.  I can often wish I had never purchased that car and instead invested the money, but at the same time, my wife and I shared a lot of great memories in that car.  She's actually a couple years younger than me, so I actually took her to senior prom in it, we went on numerous road trips, and to be quite honest, that car was as much a part of our history and relationship as anything else - and I'm not sure my financial portfolio could have given those same memories and for that I'm thankful, even if a bigger investment portfolio could have flourished into other types of memories.  Then again, according to the butterfly effect, had I invested those funds instead of buying a car, I could be writing this today wishing I had never invested into some bad stocks or something and instead just bought a sports car - who knows.

Of course, that's what is interesting about the "woulda, coulda, shouldas" of life, sometimes they may not have been the grand successes they were had we taken different approaches - hindsight is always 20/20.  Look at a company like Google and Yahoo.  At one point in time, Yahoo turned down the opportunity to buy Google for one million dollars.  On one hand, we could say that Yahoo lost out on the opportunity of a life time, but on the other hand, who's to say that had Yahoo actually taken that offer that Google would have become what it is.  Perhaps it's possible that Yahoo could have made Google and absolute failure.

Oh, and that Mustang I was telling you about.  I actually sold it this past year to fund the down payment on my first investment property and so far, it's been worth it and a part of me wishes I had done it sooner.  But I'd be lying if I told that as much as I love cash flow, there's still bits and pieces of regret that overcome me when the skies are sunny and the temps are warm and I'm not behind the wheel of that convertible.

I backed out of my very first purchase. My dad had the foresight to buy three condos so that he could sell them to his kids.  My brother bought one, installed some roommates and let them pay the mortgage. I finally decided to do the same, but between some shady dealings (my dad hiring me to create a qualifying salary) and looking at that damn amortization schedule (I don't even remember what the interests were at the time), I freaked out and backed out. (Try backing out of a deal when you're 22 and you have tell your parents you're not going to buy the house from them). They put a tenant back in, and then sold it for almost double 3 years later. Go California!

Shoulda coulda woulda bought more condos in mountain house, Tracy and Manteca. I bought a few but concentrated more on SFH. Although appreciation is not bad on the SFR but the condos and townhomes more than doubled in 3 years.

I did not know much about loan limits and local banks, so lost out on financing when I could have had a much better ROI.

Biggest was not knowing biggerpockets.com and the wealth of info on here. I was surrounded by folks who never shared their expertise nor guidance-learned my lesson there!!

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