A lot of good opinions on here already but I figured I would share mine.I don't personally have any short term rentals in NH or Florida but do have one just over the border in Southern Maine.

I see that you are a lender - any input about getting financing as a cross-border investor? 

It seems like your current PM is bordering on negligence by not only failing to get these repairs done/keep the property in shape but by failing to even bothering mentioning any of these things to you!

As has been said if you don’t have anyone local to rely on you’re probably gambling.

Any illegal activity like drug dealing, prostitution or gambling can attract unwanted elements.

- How do I convince my parent's I'm not gambling my savings?

I am a Canadian living in Calgary, AB, hoping to purchase my first real estate investment south of the border in the US this year! 

I think the known and unknown tax implications prevent many Canadians from investing south of the border. 

Even if it is right on the border of another city. 

I have 1 unit in Toronto Canada and want to look for opportunities across the border.