I agree with the basement foundation issues. I'll be addressing those probably right away. Mainly because 1 rainy spring could bring them in. Unlikely...but most certainly a possibility!
The roof has no issues yet - just looking a little ratty. No curling, no leaking, no breakage, and it has another old layer underneath it (that couldn't do anything but help, right?). I bet I can ride it out until I go. Seems like the best bet is to try to time the move in winter, when they won't look at it :)
I'd fix everything to make it the best material shape it can be. I don't mean upgrading Formica kitchen counters to granite-- I mean fixing all the current infrastructure to look as good as when it was new.
Here's why: most buyers suck at imagining the possibilities.
Spouse and I are very good at going into a beat-up house and seeing the potential. We've done it twice and we prefer to buy fixer-uppers because we have home-improvement skills. (We actually once sold a home even though we were in the middle of a bathroom renovation.) But after many hours of watching HGTV, we've realized that those buyers are very rare. Most people give up on a house if it needs work. They want to move in with just a toothbrush, not a complete set of contractor's tools.
If my spouse and I saw your house, we'd lowball you on that $10K of work. Sure, $10K might be a fair price, but there's the risk of finding out that the repair cost is really $25K. Meanwhile there's a nice home down the street for sale, and it doesn't need any work. So we'd offer you $30K less than your asking price, haggle for a while, and then go down the street to buy the other home.
Unless you know a buyer who's specifically looking for a fixer-upper, you're locking yourself out of about 99% of your home's potential buyers. After several months of this you may run out of time and have to do the work anyway-- so why suffer? Do the work now, enjoy the results for a year or two, and then sell with the knowledge that you've been living in a creampuff.