If you cannot prove income then our rental DSCR loan will be your best bet. 

I would bet the older homes will see a lot more appreciation than the newer homes, percentage wise. 

That’s the best bet. 

I think TN forgot these people are coined "Digital Nomads" for a reason, there nomadic as in readily relocate.

The Midwest is probably your best bet for a number of reasons.

My PMLs are people with self-directed IRA who are perfectly fine with 5-year term while earning double-digit returns passively tax-free in their SDIRA. 

If we face any headwinds, liquid investments go first so probably crypto but then you bet equities will get pressed.

It isn't impossible but as @Jimmy Lieu mentioned, there is a steep learning curve.Depending on your liquidity, out-of-state buy & hold rentals could be your best bet if NYC investing is out of the picture.

I think you can model a decent double digit return but how do you transition to actually pulling money out? 

If your goal is less required documentation, DSCR is likely your best bet as most everyone as mentioned, possibly a bank statement program depending on your job structure.