This needs to be highlighted in the lease and acknowledged by them.Security Deposits: You can’t use their security deposit for routine cleaning, but if they leave things in bad shape beyond normal wear and tear, it’s fair game to deduct cleaning costs.I’d start by having a straightforward talk with them about the importance of keeping things clean for health reasons and property preservation.

You have the right to enter the property to preserve the property.2.

2) Property Preservation: as the owner you have the right to protect your property - even during an eviction. 3) Monitoring Utilities: you should have been receiving the water bills.

Then cabinetry, countertops, and final coats of paint (I have the base and case pre painted before install so that caulk and paint touch ups for the nail holes are all that is needed).

They already made their money and in wealth preservation mode.Some investors are always focused on yield.Without knowing your goals it's a bunch of noise without direction.   

I’ve also read through the responses and they too are accurate, well thought out and hit the nail on the head. 

Here is an update : https://chicagorealtor.com/advocacy/advocacy-resources/northwest-housing-preservation-ordinance-issue-summary/The DOH has posted the forms required to be in compliance with the ordinance which means any properties not under contract by 11/9 will need to be pulled off the market and 30-60 days notice must be provided before listing.  

However, strict compliance with IRS rules is essential to avoid penalties and preserve the tax advantages.Best of luck with your investment!

I like the idea of investing into a program that preserves 1031 options on the back-end.

When March rolls around, I'd send a notice out indicating that to preserve their current rental cost, they would have to sign/renew their lease for the next school year prior to a specific deadline (like April 1).