I've also got a vacation rental in northern Wisconsin (between Minocqua and Tomahawk). 

A general rule of thumb though (not a hard rule) is that if a market has a prolonged history of vacation rentals such as towns whose commerce is very dependent on tourism like beach or mountain towns, then there is a good chance than those towns have established their airBNB regulations decades ago and are likely stable.

I had a friend purchase a Vacation home financed with RBC last year. 

We are compadres.When you go to any overseas place on vacation, you are going to see what "you see". 

Meaning you cannot just evict a tenant because their lease has expired.You will have to build sufficient evidence admissible in court and to the satisfaction of a judge to prove good cause to get a warrant of eviction.Many housing providers kept high risk tenants on month to month leases so that if the tenant stopped paying rent, you could simply give them a notice to vacate and recover possession of the rental unit that way.The reason for this methodology was because the HSTPA of 2019 passed in NYS made it extremely onerous and costly for housing providers to evict due to non payment.That method under good cause will be eliminated.So you can still keep tenants month to month but you will need to document the lease violation due to nonpayment rigorously.How many times and how late is “good” enough?

The mirage of get into Real Estate Investing, make ton's of money, get passive, do nothing, sip cocktails on the beach and professionally vacation the rest of your days sounds great, unfortunately it's a mirage. 

We also have a firm policy, always enforce late fees and deliver a notice to pay or vacate on the 6th.

I have not had an issue with the claw back scenario and if I did I would IMMEDIATELY begin the eviction process which I would then pursue relentlessly.But alas, some tenants use this trick after they have vacated your property. 

If I spent $50,000 on a vacation I would hope I would be treated well as well!

The PM changed the utility before the tenant vacated because the tenant chose not to leave after the lease expired.