Or it could be perfectly but it’s a gamble.

Uncontrolled water, no heat, no AC when its freezing or over 90° etc.

So that's the gamble part.

I could see Saugerties becoming more like Rhinebeck in the future (a place for people with money to retire after living in the city), but that would be the gamble...who knows how long that will take, if it ever happens (and I'm not saying I'd necessarily WANT that to happen to the Saugerties community - it's great right now in part because it hasn't become a "village disneyland").One thing I'm noticing is that a lot of places currently on the market in Saugerties were bought in the early or mid 2000's, before the crash, at pretty inflated prices.

I could *potentially* understand holding onto a property that breaks even after ALL expenses (P&I, Repairs, Cap Ex, Management, etc) if there's a good possibility of appreciation due to some sort of gentrification in the neighborhood but remember appreciation is never guaranteed so it's more of a gamble. 

Claiming such is more akin to gambling.

If your not in control of the upswing what you buy is a gamble.  

I don’t consider what I do gambling.

Holding for appreciation is always a gamble but with the run up in values in NYC and surrounding boros... holding now and counting on much further appreciation is an even bigger gamble. 

If your gambling on appreciation, that's a pretty safe bet.