@Mike Farr yeah, your income shouldn't be an issue if you work with the write lenders here. 

This might make it sound like he was a bad guy, but I think he was just trying to be an okay neighbor....He was kind of straddling that line of not doing what his agreement with the complex was asking him to do...Jon Taffer of Bar Rescue always says that people get comfortable with a discount because they come to expect it, and then get pissed when it gets taken away.

The portion reading "the party making the payments is obligated on the mortgage debt" seems to be an issue. 

Not sure what area of Iowa you're looking in, but a USDA Loan may be an option if you're looking to live in it.Good luck!

If the damage was storm related homeowners insurance might be an option?

If you are a paid member of Bigger Pockets I think they have landlord forms as well - so that might be an option.  

I would greatly welcome grabbing coffee again soon!

If allowed, it would be an Alteration Type 1 which will take a decent amount of time to get through the system. 

Bank is offering me a 4.7 APY 7-month CD which is not a lucrative offer but that would be an option.

If the cosmetics thing continues to be an issue when we tour properties together, I am considering buying a 'rental-rehab BRRR' house (like the one I mentioned at the top of this post) using my above criteria with my independent investment money, fixing it by the time our lease is up in August, leasing half of it, and trying to convince him to move into it instead of re-renting the condo for $1500/mo.