Hello everyone,I’m a Canadian looking to buy a short term rental vacation home in the Kissimmee area.Currently we own a long term rental home in Winter Garden which we bought some time ago, and will be paid off completely in Feb 2029.  

We'll lose money for 75-90 days but the new rent is market so some will stay and not forcing people that can't afford it to move in the middle of a very cold winter I think buys a tiny bit of good will and is the decent thing to do.

I've been wanting to expand out of my market in Iowa, and see that the Winter Haven, Lakeland, Haines City areas are similar to purchase points as my market.

Part of the reason coastal values haven't quite scaled to heights of neighboring states is the remoteness and lack of winter sports and high end amenities and entertainment, but that doesn't mean trophy estates, ranches and homes don't exist.

The other thing I have done especially if we are approaching winter months is just tell the insurance company that we will have them done in spring.

We'd love to escape the cold Dutch winters and enjoy a warmer climate.When we're not using the property, we plan to rent it out as an Airbnb to generate passive income.

Gas heat would require constant tank refilling and it would be very bad to run out in the winter.

Its no surprise that also took them a week to go and turn it off.I had 2 perspective tenants waiting for over a month with their national background check only to find out there were alternatives we could use to get a report in minutes but they refused to not use that company.Finally I get a tenant after 3 months on the market who is someone who was fully approved by the rent amount was 200 dollars less than market value a month so I agreed because it was just before winter when its harder to get someone in.

That was in the summer and now its winter.

The weather can certainly suck in the winter but it's no different than most of the country.I have been saying I would move out of NY for years but it is home.