Hi Adrian,I'm experiencing something similar with my place nearby (on Riverside Dr in Edgewater).

Unfortunately this is not an option for us as there is no inventory available nearby, and NYC prices are out of range... so we are shifting our perspective to possible out-of-state investing in order to get started down the path.

Are there other less expensive options for them nearby that they might buy instead?

If the interest rates come down, I can transfer the property back to my personal name, refinance, and then transfer the property again to an LLC or trust.Second and most important thing, I would like to get an idea of what type of property to purchase that best suits for STR in Chicago area , near by states like WI or MI also I am fine as long as it is closed to Chicago. 

We are getting more insurance housing requests and families staying nearby the hospital while a loved one is sick than we are nurses asking for singlets.

A great bet here is to find a nearby township that has an Ann Arbor address.

Spend some time researching nearby top-booking homes with good reviews.

What town or market are you nearby?

Nearby?

With my management skills, furnishings, and location, It leans to be in the more profitable side than I presume STRs in places that don't have major attractions immediately nearby.