The contractors work damages the rest of the structure. 

The issue I have and seen being thru several hurricanes in Florida is that once a hurricane passed and there is damage, most contractor's raise their fees as well as materials.

Recently had roof damage on LTR.

What happens when they damage something?

Are you aware that every day you let water leak in the repairs from damage the water is causing to the property get more expensive?

They kept telling me "sorry I'm gonna be late", and I didn't want to evict them with only 1 month left because I felt like they could be spiteful and do a lot of damage to the property.

You think, or feel like something works, dress it up as fact, and sell it to others.Stop doing that. 

Hey @Julie Brangenberg - I have an AirBnB here in Chicago but never in specific college towns...I would tend to say that it's probably not the best location unless you have boots on the ground there.I could also see more damage being done in college towns, higher repairs maintenance, and shorter stays but that is honestly just a hypothesisIs there a specific reason you want to get into the STR space?

Good chance a major problem - tenant non payment or damage, needed major repair, etc. puts you cash flow negative for that year.  

They will probably not cover redoing the poor workmanship but there may be some coverage for the ensuing damage (garage light repair).