What should I do with my $10K windfall, given these options?
I think you've got competition on that list for where to put the money - I'd work out which option is costing me the most currently or will cost me the most in the future and take care of it. I'd be willing to bet that Eric is right, though, that it will need to be the roof. Not fixing it could cost you more in the long run than any of the other items on the list (assuming your circumstances remain roughly the same).  General comments/other considerations: Any money that doesn't get spent on the roof (if any) - I would put in a rainy day fund.