Anyone care to share about some of their not-so-sucessful real estate investments? What did you learn from the experience?

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Good question. I still like my investments, but I just spent 30k replacing my share of a deck system, and it wasn't like my favorite thing. Don't underestimate what an inconvenience things like decks and yard space to care for an snow removal could potentially be.

Also, tandem parking invites trouble.

Only real mistake made was building in 2007 economy was booming until it wasn’t. Had 380k into the place, in 2008 it was appraised at 298k. Then 260k in 2009. Then on top of being upside down the county assessed it at 400k and said I could dispute it in a year. It raised my taxes several thousand a year. While I simultaneously lost my income. Talk about a bad couple years. I still have financial PTSD over it. Real estate does not always go up, despite the graphs and what people tell you.

oh boy. I'll try to keep it brief. 21 years since my 'first and worst' and I've got 3 rentals today. Probably bought a dozen and sold the rest. I live in Columbus Ohio - some of this will tell you how much things have changed.
"702" - $52K 3/1 ranch, purchased complete with tenant, rent was $625/mo and I had a parade of tenants, some of whom would ghost me and then leave in the middle of the night. all were hand-to-mouth. this was not Section8. I could never get the hang of dealing with the people and the people could never keep their word - I would tell them: if you have/ are having any trouble, TELL me - I'll work with you... I was not cut out for the 'hood. 12 years in, I was Done, and sold the place for the mortgage balance plus $1K in my pocket (<$30K - they added a garage and did a nice job, the 'hood was getting more bougie and sold it for $150K+. I don't care. good riddance. I did not Lose all that much, but I was not cash flowing year by year, by year. One dude even kept his pit bulls in the house and let them do their thing all over the original wood floors. That was probably the last straw, after I cleaned it out. Oh yeah this one is like a monopoly event: Water line to street breaks, Pay $3800.
The next 2 were good. $55K and $80k 3/1 homes in slightly nicer areas - $800-900 rents and mostly reasonable tenants. Sold one after 12 years, the other I still have. A few other decent ones...
"7313" - my IRA owns this house, out of state, never laid eyes on it, it's been almost 2 years, about to be on tenant #4 and the >bleeping< management company can't get it right. They will be fired in Springtime. No mortgage and no cashflow. Taxes, Insurance, vacancy and maintenance are all WAY more than the pro-forma. No real appreciation to speak of yet, or maybe I overpaid? $160K 4/2 house rents at $1400 (when occupied by a paying tenant).
Each one brought new lessons and new ways to be smarter, or to just learn to live with the pain, depending... I'll get my IRA-owned house fixed (or extract my money for a loss) and I like my 2 local houses just fine. My favorite deal was the one I got in 2004 for $55K with $7 down and some pretty minor elbow grease - the same person has been there 20 years, paying $800-900/mo with my PITI being under $500 - it's a land contract so I am a bank - don't even have to fix anything or show up, so it's a little $4K annuity for 20 years, and counting, and if she leaves, I have a house worth $140k too, and if she stays, my mortgage pays off long before her payments stop.
I just like real estate. There is risk. Not every deal works.

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