If I run out the drugs, low lifes and trouble makers and turn around the reputation, in a few years I can get rents to where they should be which would add about $4000 per month in revenue.

Is this person the decision maker or just an agent or rep of the decision maker?  

I know a company right here in Cleveland that does several of these short-term rentals for utility company workers, executive contractors, and even a film crew from California.It always charges a high deposit and much higher rents than what the rent would be to more usual, long-term tenants.The owner did not mention any issues with extensive damage, etc, but then he was trying to convince me to turn my property into a short-term rental, so he obviously wouldn't.I think if you structure the agreement so as to cover any repairs when they leave, you should be okay.

Your fourth point stands out to me: having an insider's view and watching how your specific market trends is a difference maker.

That garage/apartment looks like something straight out of a good horror film...

It's a cool little video I had filmed that walks through the work I have done and rewards I'm reaping from it.

You can watch both my interview with Ronan 9 months before closing and a second video I filmed yesterday sitting in our new condo by going here:  https://baconwrappedbusiness.c...FYI there are no affiliate links or any other payments I receive on that page. 

Know the structure of your state's real estate decision makers.

About this time I was scouting the area knowing that Lagunitas Brewery, Cinespace Film Studios, and a few other big name businesses were about to redevelop a nearby abandoned steel mill and improve the area.

I felt like you were directing your opinions towards me instead of the thread maker.