Have You Ever Regretted Selling a House?

[Julie Marquez]

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?

My first rental house, I hope to hold it forever

[David Faulkner]

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.