Since it's rare to find a buyer, the agreement expires and you have a willing seller to negotiate a deal with. 

The tables have turned and it's a buyers market now with values flat or declining, much longer days on market, price drops, listings expiring, very rare to see full price offers on new listings, etc. 

This highlights why it is also important to manage lease-end dates. 

They pay rent before the due date, clean the property after every client, and if something breaks they usually repair it before I'm aware because their clients will give them bad ratings.

Quote from @Peter Walther: Quote from @Don Konipol: Quote from @Peter Walther: I think you'll find most, if not all title insurers, will require the DIL to be dated and executed subsequent to default in order to insure. 

Here are the dates proposed.  

For the property rented in October, utilities and interest before October are capitalized, while expenses after that date are deductible as rental expenses.For the vacant property, all utilities and interest remain capitalized until it is placed in service (February 2025).

Paid platforms often offer additional features like market analytics, off-market property leads, and filters for investor-specific criteria, giving them a leg up over free options.Exactly, most platforms have to offset cost somewhere because of how expensive it is to keep the data up to date.

.✅ 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!

It will be on you to reach out to these folks to see if you would be a good match for what they need.It is *not* a site where people can just put in their travel dates and find, book and pay for a place to stay without interacting with a human.