I am pretty sure that the answer would be to wait until the spring to do this. But I will ask my husband this question when he gets home tonight and will email you his suggestions. What type of insulation do you plan on using once the new roof has been installed?
If you plan on blown in insulation I would definitively wait until spring.
I would seriously check into radiant barrier. Its a two ply aluminum foil type material.
Spending the winter in a home with no attic insulation will be a little unpleasant if you've never tried it before. Insulating the attic will make your home much more comfortable this winter, and save you money on heating costs. With an open attic as you describe, current code requirements in Michigan call for an R value of 49 in the ceiling.So personally I would insulate the attic before winter with the highest R value that you can afford, and put the new roofing material on next spring.
Unless the roof is leaking, in which case you'll want to take care of the roof as soon as possible.
My husband is against blown in insulation - luckily the attic is completely open so we can literally fill the crevices ourselves. I also don't know what r value to look for - I know I like the soft insulation - the non-scratchy kind but if the price is different, I am very good at wearing gloves and a rain suit.
I cant really gove you an answer,but what I can give you is a way to a solution, that is you have to find the anglde that you relate to or peaks your interest. A good paper is one that people get drawn into because it reaches them ln some way.As for me WW11 to me, I think of the holocaust and the effect it had on the survivors, their families and those who stood by and did nothing until it was too late.