Airbnb Help - Chicagoland

[Bruce Brotine]

Hi Bigger Pockets Community,

I already own two rental properties in Chicagoland, but I'm becoming increasingly interested in Airbnb for myself and family.  Is there anyone in the community that's open to providing guidance on how they dove into AirBnB (ideally within a three hour drive of Chicago).  My concern is buying a property around the lake communities (IL, WI, MI) and not having it filled during the winter months.  I'm looking for something my family could use 2-3 times per year as our vacation home and then AirBnB the rest of the time.

I've looked an AirDNA, TikTock (good and bad there), and YouTube videos about other people experiences, but I'm hoping to really dive into my hyper local area to understand the math and "effort" to keep it profitable.

Thanks,