Some prohibit rentals or have restrictions or maybe even implement restrictions that make your life difficult. 

You’re right about SBA’s owner-occupancy restrictions making it tough here.

You don't get taxed on gains if you lived in the property for at least 2 out of the last 5 years when you sell (check with your CPA, I am not an accountant).Otherwise, your options are to refinance (which is a bad option), or take out a 2nd mortgage, and that won't allow you to tap into all of the equity, you'll be capped at 90% or whatever lender's guidelines are that you use for that.Moving it to a LLC is a bad option unless you plan to get financing under the LLC, because that would likely be more restrictive than financing in your personal name.So although you would prefer to keep it as a rental, if you want to keep your money moving and tap into all of the equity, you have a small window to sell now tax-free as long as you lived there for 2 years before you moved out.Best of luck!

If you plan on doing Subject To or if you run into an opportunity for one, there are restrictions on what you can do.

When we were buying short sales back in 2011-2014, banks got smart and put deed restrictions from reselling the property, usually 30 - 90 days.

I think NY is just barely less restrictive than Seattle, but our legislators are hard at work at trying to fix that. 

It seems that the ordinance restricts to 60 days per year if you do not reside in the property but I am curious if anyone has found any creative ways to get around that. 

I'd set a 30 ft restriction around the property.

In the meantime, I’d be documenting the property’s condition with timestamped photos and videos from the street every month or so, and researching surrounding parcels in the county property records to see exactly who owns them and whether there are any easements or restrictions attached to your property.Given the vandalism, I’d prepare for the possibility of hostility and factor in costs for legal work, eviction if needed, and repairs.

From a tax perspective, STRs are unique because they can be treated very differently than long-term rentals, and that can open the door to powerful deductions and planning strategies as you grow into flips and traditional rentals later.Key tax points to keep in mind as you start:Short-term rental income (average stays of 7 days or less) is generally treated as Non passive income, not passive, so you may avoid passive loss limitations that normally restrict rental deductions.Because STRs are considered a business, you may be able to take accelerated depreciation or even use cost segregation to front-load deductions against your active income.If you materially participate in managing the property (screening guests, coordinating cleaning, handling bookings), losses can often offset W-2 or contractor income, a major tax advantage early on.As you expand into flips, know that flips are taxed as ordinary active income (similar to your contractor work), not capital gains.