It's a townhome that we bought to move into, but due to some last minute changes we decided to live with family and rent it out (our mortgage company is aware of this).

I am interested in living in the basement, and renting out the upper unit on Airbnb.

She's an accountant in CT, but lives in CR most of the year, so I would assume she knows some local folks.

I'm not bullish where I live, Portland, OR (high prop taxes, tougher landlord laws, affordability, etc.). 

A furnished mid-term rental or month to month lease can be well worth the small incremental monthly cost for this flexibility if you are serious about finding a great live in flip candidate on your timeline, not that of your employer's. 

Should I start the collections process while he is living on my property?

Hey everyone, here's my quick intro: I live in Calabasas, CA and I'm moving to the PNW this summer.

I need some general advice, I'm 19 and living at home.

As others have said, I wouldn't manage it, but if you own it or live on site it could work for you!

We live in a "he said, she said" world, but as long as you have everything documented and a paper trail, you're protected.