But it was winterized before they left, and the issue that caused the family to leave has finally been settled in court, and should be handled by end of summer. 

I'm looking to rebuild a network and purchase a summer home & winter rental this year.

It can be two fold on splitting utilities;  - putting all of the utilities  in the tenants name usually makes them more responsible with things and they won't be running the heat at 78* in the winter, likewise the AC at 66* in the summer and more costly bills are avoided (just examples of being wasteful on your dime)- however some investors (especially in areas where the winters get very cold) wouldn't prefer to do this as an unpaid bill in the winter may result in frozen pipes and will spilt or keep utilities in their name to avoid more costly repairsI personally would put all of the utilities in the tenant's name and just make sure I was screening my tenants well ahead of time.

I have family that live in Winter Park and Oviedo, but my rental doesn't need to be near them.

They seem to break in the very cold of winter or hot of summer because temperature puts more strain on the metal.

Vacancy rate during winter months3.)

I’ve chosen the option of turning it to my name because if it gets cut off in the winter my heat won’t run.

I would monitor it this winter and see how bad it is.  

We would probably visit our choice for a couple of months in the winter, and rent it out whenever we could other times.  

Property owners get an annual update with their winter property tax bill.