Tenants simply can’t afford them and move out.

Could simply be bad practice or something more substantial. 

What other costs are actually there that aren't coming up in my search that don't exist when simply filing for exemption?

Less people simply don't move in the winter.

Enforcing the "waste" clause (neglect or destruction of part of the asset backing the note will simply lead to foreclosure anyway). 

I ending up burning some money for the things you described (NAR membership, brokerage fees, quarterly MLS charges, etc), just a lot of things I found I wasn't getting any value from, I decided to simply put it on full stop and take a year to really reallocate and figure out what I needed to do.

Some of our owners have accidentally thought they were handing a situation "right", and because Chicago is a very tenant friendly city, the laws tend to lean in their favor, and it can cost you a lot if you are simply just not up to date on what is proper protocol (for example, what to say, what not to say, what to have in writing, and what not to put in writing, etc)... can be worth the management fees.

When I first bought this rental property, I wasn’t aiming to become an expert in real estate or accounting—I was simply looking for a passive investment.

Simply start by introducing yourself and why you’re interested in the business.

Maybe no one is an idiot, maybe they are simply being responsive to incentives.