Key is to make sure you are not cash poor.What I am seeing right now in some sub2 FB groups and a few posts here on BP is people who got close to 100% financing on properties, have a tenant in them but need a major repair and have no funds for that repair. 

When it comes to a 3.5% fha vs a 5% conventional, I personally prefer the 5% conventional because the PMI automatically drops when you hit 80% LTV.

You're investing there, paying taxes, making friends, bringing your friends and hoping to create a safe space for others to visit where the people on the other end of the line live full time. 

Companies and people/investor change overtime so it's not a bad idea to see if they're still the best fit for how you would like to see the properties managed.

So often you see a bland 'beach/ocean' themed STRs...I get it, people are booking your condo to go to the beach and relax, but you can have a fun, stand out theme that still revolves around the ocean, relaxation, etc.

People's way of doing business changed. 

Taking advantage of Section 121 and getting as much free cap gains as possible would be my route (Option 3), but you'll likely hear different responses from different people. 

But, I wonder if being an city-approved Airbnb host with a legit registration # is enough grounds to stand on legally if an Airbnb client reports/sues me because of, I don't know, a medical injury because of hitting their head on the short ceiling (even if I disclose info about the ceiling upfront on the listing).

There are quite a few people doing Sub-To and owner financing opportunities. 

Not very many people are as diligent on the hunt or as resourceful as I am.