For example, the areas economically influenced by NYC commuters: Westchester, Rockland, Dutchess, Putnam behave very differently than areas influenced by NY State employees from Albany, or farmers from (not sure?).

I'm not familiar with the USVI and Puerto Rico markets but, based on the figures given by Rachelle Bisaillon, you can get a much higher gross return in many places in Mexico with the same figures.

You should calculate the annual maintenance for an occupied property to be 10% of the Gross income. 

Actually, all of NYS (including NYC) has a maximum late fee of $50, or 5% of gross rent - whichever is LOWER.  

They are paid per closing, whereas a retail loan officer IS A 9-5 employee most of the time. 

We’re now at 30% of gross rents. 

The impact on w-2 happens if you're contributing to an employee sponsored 401k plan with that employer.  

Most people that are successfully flipping have a flipping business with either employees on staff or enough work lined up to keep a GC happy for 6 months to a year.Its a tough business to make money in when you are doing one project at a time from a distance. 

We expect it to gross $4,000 - $5,000/mo which would cover my entire PITI.What's stopping you from adding that ADU?

Since lenders can only lend up to 50% of whatever your gross income is assuming no debt.