Does anyone have roof/general contractors in Jacksonville (South Riverside/Pine Forest area)? 

If the weather were nicer I'd probably consider moving back but I certainly don't miss those winters.

@Tom Murray The rehab took a little longer than we would have liked and put us into the beginning of the winter which is a hard time to get the units rented in New York.

A few words of advice: commute times may double in the winter than in summer.

To add to what a few people have said, you see $100 transfers in many cases for properties transferred within families or for estate purposes.

We did a minor rehab on it over the past winter and I'm hoping we'll make a little profit ($10k) when comes time to sell. 

In the late winter (it may be different for you in FL since you really have no winter) many lumberyards will put on sale wood fencing.

Mass Housing's appraisal process is a lot easier too.If you can stay south of the Mass Pike and out of the Worcester hills, you'll have less snow in the winter. 

If you think it will be better to "get them out" this will give you ample time to complete said repairs, and then you will have the opportunity to find quality tenants (hopefully before winter!)

Even if the landlord pushes the expense off on the tenant, good luck retaining people when you hit them with a $200 electric bill in the winter.