This idea is like a Rube Goldberg machine built out of broken Ritz crackers and pick-up stix.

He can call for a police escort to go back and pick up his belongings.Change the locks.

Do I force the issue of the lease in keeping the place picked up?

WHAT are the ascpects yall use for criteria for picking markets and are there certain sites ?

A property on the ocean versus a ten or 30 minute drive makes a huge difference.I am a fan of doing manual comparison so you pick the comparable properties.

I know 15 people in this state and 12 of them wouldn't pick up the phone if I called (ex, former co-workers). 

Also, I would find a local REI meeting to pick the brain of those that have or are already doing this.

@Tony Freeman - What are your top chicago neighborhood picks for new and out-of-state investors and why? 

I always tell people, pick a place you would want to vacation but also consider the long term of str laws etc.

There's definitely a threshold on price and occupancy that make AirBnBs a lucrative investment though falling below this threshold by either being underpriced or under-occupied, can result in you having to pick up the tab to subsidize the property.