Renting second residence for a limited period

[Luba Vasilieva]

Hi Everyone. Would appreciate the input for the following situation before jumping into it. I recently purchased a small lake house in IL, which is sort of vulnerable to winter temps (= very lightly insulated crawl space where all plumbing is located). So right now at the end of September- I am considering two options - winterizing or renting short term (heavily under-market just to cover utilities expense) till spring. Very concerned about eviction bans should something go wrong. It looks like even a transient occupant (like roommate) will acquire tenant right pretty fast (30 days or so, but need more research). Any suggestions  from the gurus - Re: protection from worst case scenarios? Thinking finding a LT guest via Airbnb or vrbo? Winter is a low season for the lake here in IL ;)

Thank you for sharing your thoughts!