I also have several California clients who self manage north side Chicago rentals.

Just for fun, I threw it into ChatGPT, and it actually pulled up several companies you might want to check out.Mid-term rental insurance (sometimes called landlord insurance or short-term rental insurance) is designed for investors renting out properties for a month to a year.

., property management companies aren’t legally required to carry general liability insurance, but it’s highly recommended for protection against bodily injury or property damage claims.

This property has been a great experience and we have learned a lot from it over the last several years.

My recommendation would be to choose potential markets - in several price points - that have strong rental demand and year-over-year rent increases and that also are in markets that are appreciating. 

Quote from @Neal Schadler: I have several properties in Cleveland and the surrounding areas.

They are the bad guys for banning STRs or severely limiting them.  

Why on earth would you eliminate Firestone Park over several other areas in Akron?

I'm still in the process of finding an alternative solution but I thought I'd leave this here as a warning for others looking to make a decision.For reference, I'll just post their email response to me here:As we review your inquiry, we would like to remind you of the following key points from our Terms of Use:In no instance shall ShinePay be liable for any of the following:"Lost revenue from service interruptions.Lost revenue stemming from delays, malfunctions of any product.unauthorized gains access to your account or due to shared passwords or if your password is hacked.Destruction to properly, places, or personal injury resulting from the installation, misinstalling, or misuse of any product.Lost revenue from entering the wrong account number for ACH or other bank transfer or money transfers or due to any delay in receiving funds.Damage to your structure, machines or car resulting from use or installation of our products.Any funds collected that are paid to a person that does not own the property.Any harm from defeating the lock and technology that controls the lock to a device.Failure to properly service any product or machine."

We conducted several user interviews and surveys and a lot of users said that they were more interested in being able to communicate with other folks in messages and in the forums for advice.