Recently had roof damage on LTR.

What happens when they damage something?

Many variables to consider include the specific location of the home, the property manager you decide to choose, the history of the home and community, how well appointed the home is (what elements of the home will allow you to stand out in this market) and what months you decide to use for personal use.

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.

It’s a local company in Georgia elemental home 

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.  

For example, below is a photo of a boarded-up fire-damaged property in poor condition.The popular site for a rental estimates I checked predicted the rent as $2,199/Mo.

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

It also appears that there's a STRONG correlation between tax sales and distressed property (plus, arguably, worthless property) - ie it's showing on Zillow it's 400k but for the last 5 years it's been a meth lab with fire damage, or whatever.