Probably not. But I’m leaning toward it being a “thought experiment” and “a flight of fancy” as @HostAirbnbVRBO has described it. It’s not the first conversation we’ve had like this and I’ve been guilty of similar types of tangents. But I’ve been on the forum longer and have it mostly “trained out of me”.
@HostAirbnbVRBO Is something else going on? Are you sincerely concerned about this one guest sneaking her way back into another stay with you?
My suspicion is that you kind of started thinking about it, maybe because of the last guest but then it expanded and became a wider, general thought process about what happens if you end up with a guest on your property that you don’t want there. Am I close at least?
I think I can answer either way. I doubt you’ll need the information though.
So, here’s the thing, if someone/anyone comes onto your private property and you ask them to leave, they must leave. If they don’t leave then they are trespassing so you call your local cops and they will come deal with it. Tell them you have a “warned trespasser” that won’t leave.
Even better, about 1/2 the time (which really should be more often IMO, lol), the trespasser usually leaves because you’ve called the cops. Pro tip: If the trespasser leaves before the cops get there, it’s considerate to call the cops and tell them you no longer need them.
It’ll be the exact same for anyone who comes on your property and doesn’t when you ask them to leave. One possible exception might a guest who has an active booking. Not all of their guests, only the guest. In some states and localities it would be dealt with under inn-keeper law or the like. However, in MA I don’t know if STR hosts fall under that type of law (because your STR laws are so unusual). But if you have no other choice, you can cancel the guest’s reservation and then tell them to leave. Then they will be a trespasser.
I hope this helps your wandering thoughts.