If you go forward, make sure they handle all maintenance & repairs on the property too because these organizations typically have in-house staff..Snaking toilets, repairs, grass cut, snow removal, paint...Make sure you're covered with insurance as well. 

STR in those areas do well year round because of fall colors and ski resorts and snow mobiling if they are on a lake, but on the flip side you are paying significant more because they serve dual purpose.  

Saying that you are not handy in the least leads me to believe you could easily be snowed by bad subs and thus should have a good GC to look out for your interests. 

We're looking to start investing in Florida with a motivation of snow-birding at some point. 

In the Northeast that is the best time to move because you are not fighting with snow. 

I give the tenant a $100 discount if they handle the lawn care/snow removal themselves.

You'll also need a handyperson, plumber, appliance repair person, electrician, lawn care/snow removal, and pest control.

It's hot and muggy during the summer and I personally wish it had snow more than once every 5-7 years.

My kids have freedom to play safely in the snow. 

run the numbers if you snow ball one at a time and see how that plays out once it free and clear if you get there quicker ?