I realize most of the time houses in San Diego are going to appreciate but I'd rather not gamble on that.

I don't get itAs to my opinion on the subject, Bitcoin is gambling.

Some of us know when to avoid risk others prefer to toss the dice and gamble.

Im curious if there is a safe time to pull the trigger on that or if its all a gamble?

Unfortunately most MLS sellers are just looking for the highest offer and there are always investors willing to gamble and retail buyers not looking to make a profit.

$500 isn't worth the gamble of turning somebody away due to something you can't control (i.e., your neighbor's yard).

If you would reinvest it would be a seperate investment with it's own IRR.Profit is profit, no matter if you save it, gamble it away in Vegas or put in a CD.

Looking for a unicorn is a luck based strategy more akin to gambling than investing.

Relying on appreciation alone to make money is just as good as speculation or gambling in my book.

@Mian Rizwan yes it’s possible to do negative gearing however you need to have the cash to support it for 20 years.It’s also a bit of a speculative gamble as you do not know if the appreciation will be what you want.