@Christian Wathne I agreed with @Dmitriy Fomichenko , with self directed IRA options, you have more freedom on where you want your money invested in, instead have somebody else decide for you, and you also need to check how much they charge in each transaction, some investment firms are shaddy on their fees, plus you can also have others self directed IRA combined to invest in Real Estate or other ventures (*check the rules for what's allowed)  Not only self direct IRA but you may also use HSA (Health Saving Account), I'd suggest give few firms some call and get some details. 

To your comment about state and municipal debt: Are you concerned about the long-term economic health of Chi-town and the surrounding areas?

Though there is risk-return trade off, otherwise Dahl's pet rock and Google would not exist. 

No kids, pets, not a whole lot of damage to manage, mostly people looking for a quiet weekend getaway.

Sometimes there is a legitimate issue like a health issue.Unless what they say makes total sense to you, I would do whatever possible to get to the owner. 

Maybe your uncle will be great, but in the chance that he isn't, or something happens to his health you will need a backup plan or two.

What is your pet policy? 

I don't like to allow pets in the duplexes due to people being closer together.  

You are responsible for the safety and health issues in your building, and hoarding and odors like you describe are health issues (think rats) for the entire building. 

-Pet rentDepending on your building you can add income by allowing pets and charging for them.