Do you consider worst case scenario and base your potential offer based on this? 

Can you imagine your interest rate doubling like it did a couple years ago?

They all are if you ask them , its because they are getting your money .  

Also, the tenants that you are inheriting will not know what information you do or do not have.

Jeremah - First off, congrats on what you and your wife have already built—it’s no small feat managing W-2 income, business income, and rental properties while thinking strategically about tax planning.

Doing STR is a completely different game.

The payoff is worth it in the long run with reliable, on-time rent payments and tenants who are more likely to stay long-term, and take care of your property. 

It was easy to do on the lot I did it on as it was subdivided in the 1980s and was grandfathered in under the rules for then.

Even if one of you find insurance that you think covers your interest, it might be easier to buy, than cover a claim.You also run the risk of due on sale clause, because you are potentially notifying your lender in the transfer of ownership.Now I know nothing about insurance, so I could be totally wrong, but that's what I hear a lot of the nay-sayers say.

I do convert some of these people when they come back to direct bookings.