Currently, every buyer can call up any agent and they will easily show them any home available on their MLS.

They could easily be owner occupants who need a place to live.

So he owes me 20k easily.

You can't easily switch back and forth though because of the depreciation involved.

Carpet can easily get stain and will smell over time especially if the tenant has children, pets or eats in the carpeted rooms. 

But remember that house hacking can easily lead into the BRRRR strategy, house hacking is really just purchasing a home and living in it for a little while with the intention of turning it into a rental.

My Colorado peeps here can pretty easily lock down location, lol (clue: skiing here isn't the greatest).

These have potential to easily go for $100+ a night.

In CT I can easily get someone on the phone. 

Property that generates rent and that the owner has personal use of (your family member) can qualify as investment for a 1031 exchange easily enough.