New Hampshire would be much easier to start with as a it is very drivable and they have winter and summer travel seasons.

It's a great opportunity to buy them because you can get a smoking deal....but trying to sell them is incredibly hard right now.

Arbitrage was a better model when there was stimulus money and revenge travel going on.

But honestly we want to spend more time traveling out of the country the next 2 years. 

If he mentions a CT he is probably not blowing smoke and you might want to talk to a lawyer if he is pursueing things.

We have issues our tenant airbnb our place behind our back in the past, also going out of town for months on end and renting her place out while she travels, so this feels like one of those situations. 

You can deduct the hotel, airfare, Uber or vehicle mileage as travel expenses. 

The homes had no working smoke detectors (Huge liability in CAlifornia), he was under valuing the rent by over $300 on 2 of the properties, and the lease was a 1/2 page long with no rules for the tenant to follow.  

I believe I can invest and then take out whatever I have to pay the IRS next year so at least it makes me some money before I part ways with it.My long term goals are just to wealth build with my cash.I dont plan on needing anything for another house, college, etc any time soon.I may buy a car and travel but again I can take that out of the brokage account when I needed so at least it makes some money till then. 

So the rent is paid, but he is disturbing the neighbors, or stealing things, or smoking cigarettes indoors or something.