When do you decide it's time to sell your property? The advice I get constantly is to "wait" and "to stick it out", but if you're bleeding out of your pockets and still hoping that one day you won't, is it worth it?

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Investment or personal?
I would not keep any investment property that was not cash flowing (or expected to cash flow within a year)

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How would a personal / primary residence differ for you?

Honestly, when “wait it out” has turned into “I’m stressed every month,” that’s a big signal it might not be worth it. If the place isn’t cash-flowing now and there’s no realistic, near-term path to fixing that (refi, rent increase, room-mate strategy, small renos), selling isn’t quitting, it’s protecting your sanity and your balance sheet.

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