The Right Time for a Job
Roofing better done in spring, summer, fall not winter. Siding can be done almost anytime with the exception that it becomes brittle in the negative temperatures like shingles. Best time to do the inside jobs is winter and holidays.
So inside jobs can be done anytime and outside jobs better done anytime.
Now log homes where you are using logs that are just cut recently are better placed in the walls in winter since the negative temperatures are pushing the moisture out. But in case of Kentucky winter weather I ques it does not matter.