Steer clear.

Clear up.  

For me it comes down to being clear. 

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.

@Tonya EnglishWithout a clear understanding of what this company does (or more accurately, does not do), the payment seems excessive compared to other services in the market."

Building a network here can open doors to partnerships, mentorships, and local insights.3.Explore the Blogs and Podcasts: BiggerPockets has tons of content—blogs, podcasts, webinars—that cover everything from beginner strategies to advanced investment tactics.4.Utilize the Deal Analysis Tools: If you’re considering an investment, the deal analysis calculators are invaluable for running numbers and understanding potential returns.5.Set Clear Goals: Define what you want to achieve, whether it’s learning a specific strategy or connecting with certain types of investors.

A well written management contract should clearly spell out what is expected of both the PMC and the owner, to PROTECT both and avoid misunderstandings.

Currently I am looking to buy and hold for the long-term with the goal of being free and clear by the time I retire ~20 yrs. 

Just be the absolute best host you can be for the first year -- communicate clearly and quickly, make sure cleaning is top-notch, make sure all amenities work (hot tub is hot, TV remotes have batteries, etc. etc.)

Lets make that clear.