Investor · Skagit County, WA · Member since 2016 · 1k+ posts · 807 votes
This question is for buy and hold investors. My investment plan is to buy the right properties and hold them forever. For me, it's not about quantity and number of deals, but about quality and getting my few properties to cash flow for my retirement.
So my question: Have you ever regretting selling a property and wished you held on to it?
Investor · Orange County, CA · Member since 2015 · 2k+ posts · 3k+ votes
10y
I've not regretted a single house I've bought, but have regretted every one I've sold. Most of that depends on where you buy and a little bit on when you buy (or sell). I still think that selling was the right decision for me personally at the time for one reason or another (time will tell), and still did very well on those investments, but there is still a part of me that regrets it. I did learn a lot about the other side of the transaction by selling, though, so that had value ... particularly, how expensive it is to sell RE with transaction costs, federal capital gains, state tax, obamacare, etc ... way more expensive to sell than it is to buy, and buying ain't cheap.
Having said that, I think that having a pre-meditated plan of your criteria for both buy and sell is important. Constantly reassess that plan, question the underlying assumptions constantly, and adjust where needed, but still have a game plan. Also, what you do with the money if/after you sell is important. If, for example, you find a great deal on a more expensive and more long term profitable property and 1031 exchange, a sell can be great. REI is not checkers, it is more like chess ... the great players always think a few moves in advance.
Investor · Skagit County, WA · Member since 2016 · 1k+ posts · 807 votes
3y
@Terri B.@Charlotte Torres Long term vision can be hard! Wow, this thread is 7 years old and I had just purchased my first rental house. And guess what? The first tenant finally moved out today, and we are upping the rent significantly, doing a bunch of needed repairs, and I have no regrets keeping it. For half the life of the mortgage (15 year mortgage here), this guy has been paying my bills and now it's only going to get sweeter. But the more I learn from other people, I also wonder if selling to get my equity out and into something better would be a good idea too. But regardless, I'm in a terrific spot now with the rental, I enjoy being a landlord, and we will continue to hold it forever.
I think this is similar to the missing part of the buy and hold strategy for stocks. At some point you either have to sell or need to sell. At some point, you should take the profit.
I haven't read every post on this thread, but what is missing is what did the investor do with the capital? While one might say, 'oh crap I sold for $100 when in 10years it would be worth $500 now...' Well, is that after a flood came through and you had to deal with all that headache? Or, more importantly, you took the "$100" and invested in another property or leveraged to two or more properties that may be worth more than $500!!
Rental Property Investor · Somewhere over the Rainbow · Member since 2021 · 1k+ posts · 1k+ votes
3y
I see a theme here of: "Yes I regretted selling because I bought for 200k, sold for 300k, and now the house is worth 400k"
So this is generally true with just about anything other than used cars. My stocks went up over time. The gallon of milk at the store I bought went up over time. The house I bought in 2022 sold for 42k back in 1975...
Other than the covid era where you could have bought anything, held it, and sold it a year later for a massive profit we are seeing a general appreciation here in real estate as far as value is concerned. I think that's hardly a regret for selling because that "appreciation" is generally inflation at work (yes some will get lucky with massive appreciation based on their location but I am talking about the generality here, which is seeing ~3% YoY). I guess what I am saying here is that regretting selling something, because the value went up after you sold it, is not a regret unique to real estate...
I think the better question here is: Is there a reason that you regret selling that is unique to real estate investing?
Do you miss the tax dedcutions?
Was there some effect of selling that you didn't realize until later?
I bought a sfr tear down in 2015 for $100k, sold it 3 months later for 120 because the neighbors were using it as a parking lot and sh&tting their dogs there, and, the city in that area requires an in house sprinkler system for new construction. headache. Should've boarded it up and waited. $500k just for the dirt today. I'm mr buy and hold normally. I'm taking my sfr's with me to the grave. Not gonna pay cap gains and recapture, no way. When I kick my kids can have all that new basis. I'll rest easy knowing it.