1) Although I train in Clermont and currently live in Winter Garden, FL, I grew up in Toronto and went to school in Los Angeles, so my familiarity with the Central Florida area is limited. 

Last year may have cost $600 hiring out but ask what it cost them in 2014-15 winter.

The only thing that worries me about that is a tenant moving out during the winter months and me being stuck with a vacancy until the spring.

It'll be interesting to see what this winter brings.  

Great skiing in the winter and hiking/mountain biking in spring, summer, fall.  

Does anyone buy land before winter?

Anyone out there have any experience with condos in Colorado ski towns such as Avon, beaver creek, or winter park?

. :).I had one tenant who could not pay rent and heat so I said no problem don't pay rent through 3 months of winter and then we will just add it to the summer rent.. well end of three months they just move.. 

We've made strong money from the sale of our first house thanks to my hard work and our good fortune; and now we find that we have the money to flip a house over the winter.

Make sure they are changed before winter comes.