Ever feel like you killed the goose that laid golden eggs?

Have you ever regretted selling off a property? I can think of a couple of cash cows I unloaded years back, and I often find myself wondering what might have been if I’d held onto them.

If you’ve ever been in that position, what was your property? Why’d you sell it? Why do you now regret the decision?

@donyost - I'm not sure if I "regret" it per se, but I sold off two duplexes last year at what I thought was near the top of the market (both of them had tripled in value since I bought them in 2011 and 2014, so it wasn't an unreasonable conclusion). Since then, I've just been watching the market get hotter and hotter... so part of me wishes I had waited.

I don't think anyone can time the market perfectly, but I came out pretty well in the end.. At some point, you just have to take a leap and hope for the best.

In my situation, these rentals were just providing some additional bonus income, but I wasn't getting rich off them, so it wasn't that hard to part with them. If I had sold off a huge apartment building, I might feel differently.

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Just about every house I have flipped, with the exception of a couple in rougher neighborhoods could have been positive cash-flowing properties that i would gladly add to my portfolio now.

Which is why I know keep the good ones and offer those questionable ones on lease options.

I'm selling my cash-cow property here in NY because the market is up, and I'm getting closer to retirement and relocation (too expensive and cold to retire here). It's paid in full, and I'm making a decent profit....not as much as I want, but it gets me out of the headache (bad neighborhood), and gives me a load of cash to invest in land and small private loans to flip investors that I trust. I'm planning to do only land going forward as a retirement "hobby" and income. I love the RE business (especially land) and will probably do it until I can't anymore.

I guess I'm in a seller's remorse mindset right now, as the cashflow was/is very good. But, because of the neighborhood, I'm justifying the sale to myself (and all of you) while at the same time feel like I'm killing a fat goose. :)

Happy New Year!

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