Bankers are pretty sophisticated these days with the advent of the computer and all and there's just no way to make income "look" like something else. 

Most banks don't like 2nd mortgages, anyway, and one that leaves no equity doesn't make sense in banker world.

@Kerry Baird makes a good point - don't forget to factor in closing costs, they are high in NY state (you've probably already thought about them but a good mortgage broker/banker will give you a written estimate that should be close to what you pay at closing). 

@Nathan Winslow @Parish Simmons Bankers will most likely say that they don't allow it.

The best game plan is to start having conversations with a Banker or Broker to do a Fannie Mae cash out refinance to get your original investment money back out so you can rinse and repeat. 

Unfortunately you're a little late to get in on it, but Duluth did break ground on a tiny house development project in the summer of 2021 that awarded free lots to contractors to build the structures on and they might do it again in the future, so might be something to watch out for.If you're looking outside of the city and up the shore where most of the tourism occurs, you might be able to find something more "affordable".

Also talk with your banker if you plan to Cross Collateralize anytime.Also read the "S" corporation articles and any operating agreements.Sounds like you have the numbers analyzed. 

Ask your network for referrals for accountant, agent, attorney, 3rd party property management, and banker.

I'd highly recommend building relationships with many different commercial bankers if that is who you are working with for the refi's unless residential.You can definitely build relationships with local bankers, credit unions, and mortgage brokers for commercial refinancing.

Just need to have a good mortgage banker on your side and of course you are going to have to do a lot of legwork to find the right property.