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What should I do with my $10K windfall, given these options?
Have you looked at DIY roof repair?  Caulking with tar adhesive, and shingle replacement isn't that hard, if you're in good health.  Totally depends on how bad your roof is/what the demands on it are going to be.   If you can squeak another year out of it, with minimal investment, you'll have a year's worth of, say car-debt (at what percent interest?) to put into your roof fund.