The previous Tenant left the place dirty, and several rooms need new paint.

A lot of the top places have seasonality issues so don't let it scare you.

I would review your management agreement but the only one that seems out of place to me is 8% for the water bill

.✅ Professional Tenant Screening – Property managers have systems in place to screen applicants thoroughly, reducing the risk of bad tenants.✅ Knowledge of Chicago Rental Laws – A good property manager stays up to date on local laws, helping you avoid costly legal mistakes.✅ Maintenance & Repairs Handled – No more emergency calls at 2 AM about a broken water heater!

I asked the question so I could make sure there weren't scenarios like this I wasn't considering.For context, I'm not talking about historical homes in places like Martha's Vineyard.

You can see huge homes being built all over the place there now.

Tenant will move out for a bigger place next month.

I have NOT placed much research into it but from what I have read their fee structure is expensive. 

You all not be able to raise rents 50%, the renter in place will not be able to afford it.

Meetups - Our events page is a great place to start, some areas of the country are far more active about posting their meetups than others, if you're not finding anything here meetup.com is a great place to look as well.