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).

It fixes some of the issues above and preserves capital.

Excessive complaints or three violations in three years could lead to losing the ability to operate​.Impact on Neighborhoods: Non-owner-occupied STRs (Type 2) may cause friction in residential neighborhoods, as they often function like businesses, which can disrupt the local community atmosphere.Recent Regulations (2024 Updates):1) STR operators must obtain a permit for either Type 1 or Type 2 properties, depending on whether the owner lives on-site.2) Platforms like Airbnb are required to remove any listings that lack a valid permit.3) New noise and occupancy regulations apply, with stricter enforcement through permit revocations and finesThese regulations are part of the city's efforts to balance the benefits of STRs with the preservation of neighborhood quality and local safety standards.4o

For instance high net worth investors may want "A" location homes for tax benefits and wealth preservation.

@Dan Thomas hit the nail on the head with data dashboard’s broad inaccuracy in rural areas like New England.

I think @Jay Hurst nailed it on the head.

thanks Michael -I think you hit the nail right on the head . 

As mentioned you also can hire a property preservation company to come winterized it as wellAt this point in time it shouldn’t need to be winterized in Chicago but it’s always good to look and think ahead.

Once you've got your market nailed down, that's the time you build your local network.

Why are you trying to nail down an exact time?