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There are a number of variables to be aware of depending on the work to be done and the current weather. Some are as follows ...
If the roof is to be 'opened up', it should be minimized to prevent the 'outside elements' from getting in. If the 'space' below the opening is a finished room (vs. an attic), then yes, you might want to wait for warm temperatures.
If the space below the opening is an attic that's UNFINISHED, then as long as the opening is covered at night or during bad weather, it can be worked on at any time. Of course, once the opening is made, it should be finished off as QUICKLY as possible.
Now, to make things more complicated, if the fix needs to be done ASAP, then it should be. I can't make that call. If, for example, you have a leak, you might want to have it done now because, over Winter, that water can freeze and cause MORE damage to the roof AS WELL AS to the inside of the house.
If your Contractor has been in business for a while and came referenced, then you should be in a decent position to trust his judgement. My best to ya and hope this helps.
Jay J -Moderator
PS: God Bless America!