I bet realistically most people would stop there.

I don't think we will reach those lows again, but wouldn't necessarily bet against it, either.If you are skittish now, I'd get it on the market right now while there's still a season left, and price it to MOVE.  

I bet you could quickly get an idea about financing, insuring, and feasibility from them.

TIAErich your best bet would be to amortize it over thirty with a 5 year balloon. the issue with private lenders  vs. banks is private lenders use their money to lend and many times it may not keep up with inflation - so lending for that long does not make sense.

Also remember the time these returns will take to amend along with the possibility of opening up audit periods/red flags with the IRS due to amendments.Doing this yourself on turbo tax likely won't be your best bet considering all of the details.

If they don't have one, I bet they know somebody.Answering your questions:1.

This seems like my best bet at the moment.

Most of the regs prohibit it within the city, so I would check and see if the area you are looking allow it.Your best bet is to look at the markets on VRBO and AirBNB and see what is out there right now.

I am betting that there aren't that many STRs that offer a setup like that in your area. 

We opted for option 3 for the safest bet in a stagnating market and tight funds.