This can be tricky and a gamble. 

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

I do not recommend buying in Hartford, as mentioned most areas especially, the areas zoned multi unit, are rough and border line war zones.

I am not a gambling man.

We just purchased the ground floor in the last year because the location is A+ (borders a park, $1-$3MM+ homes all around.  

@Matt ScholtenI am Canadian and buy/sell all the time cross border and quite often am in Canada for closings.  

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.