In the long run, you should see cashflow go up but you probably aren't going to retire off cashflow in the early years, even if you bought a coupled dozen properties.So, if you want to dip your toe in the water the easy way, start with a turnkey rental. 

Most can't do it because they are looking for quick money and don't want to do any work are aren't really in it to help people.

Window units aren't a deal breaker unless its a larger unit.

STR's aren't impossible here, but depending on the area, you'll find them to be extremely seasonal.Other strategies that have worked for me and my clients is the MTR route, there's a robust hospital system in both NYC & LI that is always hiring contracted nurses for 3-6 months contracts. 

It doesn't mean there aren't more to come.

Investing in rental property in NYC and NYS be very profitable for 2 kinds of investors, very large investors owning 150 unit or more apartment buildings that aren’t in the rent stabilization program and very small investors owning duplexes and living in one of the units.

They aren't going to pay for closing costs, they are going to want something around 8-10% interest, HML is around 13% right now and if they doing 7 years, they would want a lot more down payment than $10K. probably $30K

The buildings are still old and aren't fancy but they are clean, livable, and give them some sense of pride in living.

They aren't dummies.

That's a very subjective issue.I would want to ensure you aren't missing the outside.