I've noticed that roofing contractors in the area are pretty busy and they are pushing to get all their projects wrapped up before winter right now which can have an impact on price.  

We live in Charlotte so my target is Blowing Rock/Boone for convenience to Charlotte, skiing in the winter, cooler temps in the summer, etc.  

I'd like them gone ASAP, though, so I can repair and raise the rents, and get it turned over before winter.  

Also not sure if that is wise given the winter months are around the corner which are not ideal for trying to rent an apartment.  

I would just say that if you're going to get a rental in December just something to think about during the months of November-January there is generally less demand for housing as people don't really like to move during the winter. 

@Dan Pezzano This Friday MassRealEstate dot netYou may want to focus on this Winter, I usually pick up a deal in January and February, when no one else is looking...

I wouldn't last one winter in your shoes! 

I wasn't sure if I can raise the rent a bit to cover myself for the winters or try to zone by ripping out the boiler and installing central ac and heat in basement for unit 1 and ac and heat in attic for unit 2.

These should be on the tenant and they should revert back once the tenant vacates the home, this is especially useful when the winter months set in and the home is empty.

I do have to say, I don't miss shoveling snow every winter at all.