Wow that is interesting of all places to ban them. 

b. an expense put on the LLC's tax form (8825) and split 50/50 on the partners' K-1s?

@Katharine Gonzalez @Katharine Gonzalez I think the best approach is to first make sure it make sense first as a regular rental property especially with all the rules governing what the city bans them and you need to convert to a regular rental. https://www.airdna.co/airbnb-calculator

A short term rental unit is only a few bad reviews from being ruined and one bad piece of legislation being passed by the local government banning them. 

@Matthew Meunier Although you'll see many STR's advertised within Naples, and Collier county as a whole, it's important to know that they both have completely banned personally owned and operated STR's, so you would be in violation of those ordinances, and at risk of legal prosecution if you were to purchase and operate there.

Due to affordable housing shortages, Some European cities, like Frankfurt am Main, have restricted and/or banned short-term rentals like Airbnb.

In Canada when they legalized it, landlords could still opt to ban smoking it in the rental units as part of their leases.

According to a recent report, corporate buyers own about 3-5% of single-family homes in the US, but that number could increase as they see more opportunities for profit.Some lawmakers are trying to stop this trend by proposing a new law that would ban corporations from buying single-family homes.

You agree that listing or advertising the dwelling on Airbnb.com or similar internet websites shall be a violation of this Addendum and a breach of your Lease Contract.TENANT(S) shall be solely responsible for getting notified of any municipally or town updates that would affect their use, including but not limited to: declared parking bans, updates of trash / recycling day changes, and the like.

They are discussing a winter ban on evictions so I would make sure they do everything they need to do to get this guy out.