Finished basement as well with additional room (and has the additional bathroom). 

This home is not a luxury home so the insurance route seems overkill.2) Buy a worry free waiver and add it to the booking rate?

This reminds me of the story of a wall-street banker convincing a fisherman who already has time for his friends / family to instead scale his fisherman business(get employees, integrate, then sell the business) all of which will lead him to be able to spend time with his friends and family.It already sounds like you have a great life - spending time wth family and in great health.Having additional money doesn't sounds like it would improve your life that much.

(in terms of pros and cons).You can also use rentals to provide additional borrowing power if your rental currently cashflows from a tax perspective.Hopefully that helps your scenario advance forward in terms of what to ask and think about.

- We had 2 break-in & furnace & HWH thefts there this year:(File a claim ASAP, you'll need:1) Utility bills to prove electric & gas were on2) A police report, proving a break-in3) Pics/video to prove the condition of the property to support theft claimWhat are you doing to mitigate additional damages?

A factor is whether the panel and electrical can handle the additional load.

In addition to checking Airbnb monthly rates, I checked the MLS to see what monthly rents were.

Doing additional payments will shorten the life of your mortgage and save you a lot in interest. 

Install additional stackable W/D units in the garage (requires some electrical work).2.

Worst ADU addition appraisal occur where there is no zone MF in the vicinity.