My wife and I rent in Newport Beach CA during the winter...But we OWN 131 rentals here in Metro-Detroit!

@Joshua Biondi  You don't need a 24 hour handyman but you do need a 24 hour HVAC service if it gets as cold in winter as here.

Mold was caused by shallow groundwater/excessive rain last winter.

I live in the northern part of the country with long winter/wet seasons.

HITS Ocala used it be one of the only winter horse shows accessible to the middle class. thousands of families (daughter and moms or one mom with all the kids from one barn) from the Northeast and Midwest head down for anywhere between 2-12 weeks beginning in January.

The market does slow in the winter, but people still move, especially in areas with decent weather.You need to study the market constantly and know how you compare to the competition.

You'll have periods of vacancy during summers and winter breaks, so factor that in.  

I don't know the intricacies of how they are installed or if one is cheaper but I can say with 100% certainty they are going to be better in the snow/winter and extreme weather. 

Also, consider the location within the resort -is the home strategically near the clubhouse, or does it have a great forest or lakefront view?

I'll watch a game down there - just fine then all of a sudden I need 2 sweaters and a winter hat.