Put another 50% down on a vacation rental somewhere fun (probably the Caribbean).

It probably only rented 65% of the time in the winter (Ice Carnival time was always booked); however, the real issue was spring time when skiing wasn't good, but boating/mountain biking/golfing/hiking was still too snowy and muddy. 

The black and white modern farmhouse styled mobile home is freshly painted outside and pops with a Caribbean blue double door that opens up to a spacious 1100 sq ft of interior living space.

The local bank did allow me a mortgage and accepted my proof of salary to do so.The property is a SFH and is in long term rent, eventhough it has a strong short term market.There are Caribbean islands that give investors perks which could even go as far as a passport.But mortgage is not always possible and worth checking out once you decided your market.Short term vs long term is also worth looking into.

Considered the "entryway to the Caribbean," Miami has a cosmopolitan character formed by its extensive Latin American populace that pulls in investors to the area, and draws investors from Western Europe and other foreign markets.#2 Jacksonville, Florida Contrasted with a considerable lot of Florida's other huge urban areas, Jacksonville is a lot calmer and does not have the gigantic herds of tourist guests.

Good Morning Kent,As a fellow Canadian that years ago escaped the harsh winter years ago, I would like to suggest to you an option that is a favorite of a growing number of Canadians AND folks from around the world....TURKS AND CAICOS ISLANDS...ranked the #1 Beach in the World and the Caribbean by TripAdvisor. 

That looks like something out of a Carnival Fun House! 

I do feel blessed to live in America and I have traveled around a lot of the Caribbean and to a few countries in South America, amazing places to visit.

We both want to travel, live in the Caribbean during the winters and on the lake in the Midwest.

 I was wondering if anyone has experience with traveling to the Caribbean or buying properties in the Caribbean.I am wanting to purchase a vacation home, and also rent it out when we are not there.