Some people say buy no matter what, but that doesn't sound like investment strategy, it sounds like gambling.

I am not a gambling man.

When i started i took a gamble on Williamsburg before it hit,it worked!

That is literally just gambling......I'd be very hesitant to want to have my money tied up in something that is so unregulated and that has so little control. 

I'm no good with a hammer, not interested in flipping which seems too much like gambling at this point in my life.

If we ran it for a year and worst-case a renter who's unhappy with us attempting to raise/normalize rents reports the leaking roof, we could be stuck with MAJOR repairs that we can't yet afford, or who knows, a condemned building because there's mold in that roof/attic/walls that have been leaking.It's discouraging - we could walk away and take our $25k and go 20% down on a duplex that cash flows $300 a month, or we gamble on this place where the cash flow is approaching $1.5k per month after budgeting conservatively with the bigger pockets calculators. 

Your play here is gambling on appreciation hoping you make your money that way which is just that gambling. 

I got all my families' money out of that speculation and gambling game.  

Offshore capital has landed and increasingly seeks the safety of gateway metropolitan investments.

Sell to my long-term tenant for $400,000, and invest proceeds in stock market, while avoiding new roof expense in a year or two and taking a gamble on new tenant when current one leaves if I don't sell him the house.2.