I sent you a DM if you have any interest in the Midwest/ MidSouth areas to explore some options so you can have an idea of what it may look like to execute your plan!

If you include a low-maintenance marketing plan into your vacation rental, you’ll attract high-paying guests without constantly grinding to fill your calendar.I’ll get back to that in a minute, but first—let’s talk about your reviews.

I had hoped to offset it with my capital loss carryover and haven't planned for any expense documentation etc. can I make the case that I am not a dealer because this is my first time and also have a high w2 income relative to the LLC profit? 

Have you discussed your plan with any social service organizations and/or impact investors (i.e. foundations and philanthropic orgs) in NYC that are looking to help you?

Also confirm if its a planned community sometimes they have multiple HOA (master and local) that this can fall under. 

Current tenants are coming up 3 years in the house with no plans to move.

you may have to save up until you have enough money to do so - down payment, closing costs, reserves, etc.House Hacking: What Is It, How to Start, and Strategies for Successit's a more powerful way to get started. 

It will save you time and effort. 

Make sure your lender supports your long-term plans, as refinancing early can be tricky with DSCR loans.

If you buy in a city with limited appreciation, every investment dollar must come from your savings.