Prices did seem better than DFW, but about 5 years ago when it was on my radar, I never found an area where I thought there was good balance. 

Just a thought.If PMS or escrow accounts seem like the best path, could you recommend specific tools or platforms to streamline these processes?

@Eric Chappell this software does seem pretty cool.

I’ve got 29 SFR and this seems to be quick and easy to do.

One thing I'm trying to do is to test different cover photos to see which ones draw a greater % of click-thrus (which seems like a reasonable thing to test).I'd like to be able to view the Airbnb stats to see, for each cover photo I test, things like what % of people click through on it.

Or else reduce enough on price to deal with an eviction from an illegal unit.I don't know Chicago laws, but in NYC if you have an illegal unit, the tenant occupying it seems to have more rights than the owner does and doesn't have to pay rent... 

(I apologize in advance if this reply seems a bit lengthy.)

But it seems like a very Californiay kinda thing to do. 

I've done extensive research into the options and a lot of the paid options seem to focus on teaching specific investment methods.

It seems that the tenant has been there for a year or close to a year, probably since you bought the house in November 2023.