If you are a control person, this can be a challenge but I have learned to let go over day to day issues that come up that I would do differently.Handypersons are a tough one.

With @Michael Baum on this.Another angle of thought - who would have a better chance of success challenging Airbnb TOS:1) A "brand" with 5 units2) A brand with 500 units?

Knowing you have someone to turn to for advice and validation can make navigating challenges feel less intimidating.5.

I wasted too much time trying to piece it all together and when you're in different states it's all the more challenging to make sure everything is legit.

There's a good chance the issue(s) you face has already been discussed and answered.Ask questions in the appropriate forum.

Hi @Jacob Dalton,Thanks for sharing your situation—it’s clear you’ve put a lot of thought into this decision, and I can understand why you’re concerned given the challenges of being a landlord in Cook County.Screening tenants is definitely a key step, but I agree it’s not foolproof.

That experience taught me to always overestimate CapEx and vacancy buffers... it’s much easier to sleep at night when you’ve got those cushions in place.From what I’ve read in Bloomberg, these challenges aren’t unique, especially with rising rates.

The test were very difficult and challenging. 

Your journey into short-term rentals sounds like an exciting shift—I can feel your energy for taking on a new challenge. 

Challenges?