Tell him a move-out date that he must be out, and if you show up on that date, all his stuff is out, house has no damage and is in broom-swept condition, you pay him x amount of dollars to give you his keys and leave peacefully.

The pictures below is a map I use that shows me where the property is and also who the councilor is in the area, what's for sale in the area, what part of town, and when i click on the property I can see the last sale date, how much it was sold for etc...I'm mostly in the North Shore and some of these city halls are a bit outdated but the people are very friendly at least.

Another one is outdated and rents for $700/unit.

Here is one of the threads that @Ann Bellamy was mentioning, and in it she even remembered the title and author of one of the few books on this subject (and some of that book is now out-dated):https://www.biggerpockets.com/forums/49/topics/79786-how-to-learn-more-about-becoming-a-private-money-lender

6-8 months are not valid comps, they are outdated ones.

A lot of the homes close to the university are old and outdated but the area is low crime and very accessible.

The only recent sales are 60-100 years old and very outdated.

There are a lot of real estate courses you should look into (some info may be outdated but you can learn a lot) Here is a link to one of the courses from MIThttp://ocw.mit.edu/courses/urban-studies-and-planning/11-431j-real-estate-finance-and-investment-fall-2006/That one isn't necessarily what a real estate agent would learn, but there are many more courses out there.

whereas the older ranch homes are typically smaller and usually outdated..   900 - 1100 sq ft.  

I reported that to the guest, so then the guest called AirBnb and this is where it gets interesting: AirBnb rules allow guests to "amend reservations, but not cancel them" as long as they are greater than 30-nights away from the check-out date and the host does not have to approve the change.