There are numerous ways to increase your knowledge.  

They have numerous properties free and clear, thus the need for the LLC and asset protection.

However, the things that made me question my future involvement with this unit were possible big expenditures like all the water lines being made of iron (nearing the end of their usable life before cracking on this 1960’s house), a giant tree root running through the center of the crawl space (could disrupt foundation further), or numerous large pine trees either already dead with limbs hanging or leaning over the roof that needs replacing already.

Even though the suggestion is out there the reality is that I shouldn’t expect folks to do this all on their own dime in this market.I didn’t want to pay for all or even part of numerous inspections, that could add up.

There are numerous other strategies out there, but these are the most common and straightforward.

Class A props won't cashflow for 3-5 years, unless you buy from distressed seller or can reposition and raise rents.Class B is really where most investors want to be.Class C is usually NOT for newies, due to numerous challenges that will cause panic attacks.

Landlords or property managers send out the notice to vacate, not courts.  3-day for non-payment.  30-day for other reasons (too numerous and not relevant here). 

The suburbs of my city (Chicago) have numerous cheap properties that are burdened by high taxes.  

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.