In addition, there will be a ton of high school seniors coming to campus Jan-March to tour campus etc to decide if they would like to attend etc. 

Usually companies are charging 10% on top of maintenance repairs, in addition to one months rent as a placement fee for leasing unit.

After we gave him additional time to come up with the money (a mistake I know), he said he COULD pay, but that it would only be in cash (not in the lease) and we would have to come pick it up.  

I could see how purchasing before the rehab I could have added additional equity but then I would have had to manage the purchase and rehab from out of state.

In addition lower rents will decrease the value of a property, not necessarily its appraised value, because no buyer will desire to pay retail for properties with reduced cash flow.

I'll echo what Zeke mentioned about interviewing multiple realtors / PM's / Contractors to make sure you can get a good idea of what the area is like, in addition to working with someone you're comfortable with. 

Additionally, I wholesale deals and we buy & hold in SE Wisconsin.

Obviously do your own research before asking people on Facebook, but just another way to connect with hosts and see what they do and how they file those STR taxes and maybe some additional helpful info. 

Quote from @Mitchell Gunlock: Quote from @Cliff Benner: Looking for Tips on how to find places that have multiple cabins or additional dwellings on a property that I could live on and run.

Feel free to message me if you have additional questions.