I STR it for 15-20K a month in the summer, and was offering it for rent for $2100 a month in the winter (lower than any comparable houses), and was getting tire kickers at that price. 

To resolve this as quickly as possible, you can either choose to level with the person and see if they'll agree to move out on their own accord (you may need to offer concessions) or get an eviction attorney involved.

-- Also, if they are really pushing this as a benefit, what type of guarantee are they willing to offer to back it up?

Another would be when a lender or bank offers you the cash to buy the home and they cross collateralize one or more homes to bridge the gap of equity needed.

I guess the next step would be to find lenders in my area that offer these types of loans.

Quote from @Thomas Haessig: I have two accepted offers to buy and house hack.

Best software in Florida REiFax, all the information and tools you will ever need. from finding cash buyers, and absentee owners with more than XX% of equity to send offers. 

This helps keep demand for rental properties high and offers some stability for investors.

That kind of restriction just doesn’t work for someone like me.I’m trying to figure out if I might be missing something in how I’m approaching this or if others have insights or examples of towns that not only allow STRs but also have laws that offer enough flexibility to operate in the way I’m aiming for.Many towns technically permit STRs but impose restrictive rules like membership requirements, ownership duration limits, or rental day caps, making operations challenging.

That on top of the tenants' usage, what speeds would you offer?