Assuming I am understanding you plan.

Pretty solid pocket it my opinion

Proper Insurance and Steadily have always been solid options for short term rental insurance.

We don’t fully understand why it hasn't dropped more."

We received the payout in about 30 days and were able to rehab the unit and get it rented again promptly.From my understanding of the situation, if the tenant did not have the renter's policy in place, our own landlord policy would most likely have covered it, but they could also have pursued the tenant to collect those damages.

I understand that you want to look for a place with year round tourism, growing tourism stats, favorable STR regulations, etc.

I'm well aware of the challenges ahead and understand the importance of making informed decisions.

If I factor in additional $5,000 in upgrades it still hits a 30%+ CoC return....It certainly is not a grand slam, but for the extremely low barrier of entry, it seems like a solid base hit. 

If the property manager is named on the contract, then the property manager can represent the owner in court.This may not apply to your situation, but I highly recommend you read the law or speak with an attorney to understand your options and which method is best for you.

Much easier to when you start with people who understand the question.One way a friend does this (not USA based) is to set up joint ventures.