Should i sell my rental property now or hold for long-term cash flow?

[Ryan.J]

I'm trying to figure out if I should sell my first rental property now that the market's high, or hold it for the long-term cash flow. The capital gains tax hit from selling feels substantial, but I'm also worried about missing this peak and facing major repairs soon.

[AveryQM]

I pulled the trigger last year when offers looked strong. The capital gains tax hit was huge, and the depreciation recapture sting was real, but I slept easier knowing I wasn’t staring down another round of big repairs for the next decade.

[Sofia.L]

I kept mine for the cash flow. Rents stayed steady, mortgage paid, and I could chip away at a few cosmetic upgrades. It felt less dramatic than selling and wondering what comes next.

[Matthew.J]

Part of me wonders if the real issue is maintenance and debt service more than the market peak. I tried timing it once and ended up with higher vacancies and more patchwork than profits.

[JasonG]

A quick scenario could help, hold for a year and compare after tax cash flow with a sale now and reinvestment, but I’m not sure any model captures the gut feel of a big repair bill.