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.  

Putting hard money down on Day 1 is foolish, and no better than gambling.

@James Wise Which I understand is a gamble. will probably just wait on a 3-4 unit and house hack with the Va loan when the right deal comes up.

U cannot understand the risk in some of the mid west deep south north east without going there and seeing for yourself.but if you simply want SFR's every city has a median price point.. we have one here in our area for SFR which is closer to 350 to 400k but like say INday for instance its 130k.. you buy at the median and your buying were homeowners are buying and some investors. you buy at 75k and your in an area that ONLY investors buy in.. and your values will ONLY be worth what the cash flow is. its all about balance.. risk reward.. and of course I don't subscribe to the cash flow is the only thing and appreciation is gambling NOT at all.