The tenant has caused damage and broken the lease so she is going to vacate in December.

Often, safer to file with the understanding those fees may be wasted, but better than waiting and then the tenant does NOT vacate (causing more lost time/rent).Usually court date will be 2-3 weeks after filing, which means 1st or 2nd week of following month.

This is a possibility, but I’m not so sure we’d enjoy living in a multi family.

I would look at what your strengths are and what you enjoy.  

Flips, BRRRRs, vacation rentals, etc..

I'm particularly passionate about central Florida, where we use to live and where we currently live.Outside of real estate, I enjoy flying as a professional pilot, spending time with my family, and traveling.Excited to learn and connect with you all!

You can search your local area to establish comps through visiting various short term vacations sites (Verbo and Airbnb).  

When he vacated the property and returned to his home state, he left under hostile circumstances and left significant damage at the house.

If I buy a vacation home using a 2nd home loan and rent it as an AirBNB when I am not using it, can I still do a cost segregation study to accelerate depreciation and offset losses against my W2 income if I follow the rules of STR tax loophole (I.e., the average stay in the house is less than 7 days, I manage the AirBnB myself, and spend 100 hours or more a year and more time than any other person/entity on managing my AirBnB business)?

I mean, they are technically a squatter themselves so why not just put another squatter in that will make them miserable wow keeping them from damaging the property who will then vacate the property whenever that one’s gone.