Your story of "bad" financials that banks laugh at is all too common.

So, that suing after the return of the deposit is possible although probably not common. 

Additionally you can contribute 20-25% depending on the situation of what you pay yourself or the gp of the company which is commonly called profit sharing, which you don't have at your w-2 job and your w-2 job has no impact on this. 

I've been at the property a lot in the last couple of weeks, and tenants are telling me that a group of teenagers will bust through the common entry doors and steal bikes and things in the hallway.  

That's the one scenario for HELOC interest deductibility that the TCJA left in!

I'm assuming it's a big building so that would be something you should review in the by-laws in terms of what you're entitled to.I would get in touch with your personal accountant/CPA or perhaps a local real estate specialist in NYC (there's a few in the forums) regarding your scenario.

That property is literally screwed.The real answer to your questions is it depends on what is common and accepted in that area.

Rochester has a lot more in common with Buffalo than, say, Troy or the Hudson Valley.If we're getting that specific, there are a few more areas to consider.AdirondaksNorth Country - Watertown, Potsdam, etc.Long Island (very different than NYC)The Finger LakesWith that many regions, I think it's better to just use city names rather than regions.

With Austin being a hot market, you could lose out on a lot of appreciation.If you wanted to get some numbers to think through the different scenarios and tax implications, I would recommend consulting with an accountant/CPA!

This is common in my area/Colorado in general especially the ski towns that still allow short term rentals.