My two cents on the resale values; this is the time of year when convertibles sell, and I'd have to think it's not the time of year when I'd want to buy.
I haven't exactly done a trend analysis, but I'm pretty sure a $20K car in May is a $15K car in December. A $10K car now will be an $8K car this winter, assuming that follows.
If I was looking around to buy one, I think I'd stay away from the chopper-gun fiberglass like my CMC body has (the difference in overall finish was pretty evident to me while I was asking questions at the show this weekend), and I think I'd be looking for one which has been professionally prepped and painted. The Gelcoat finish mine used to have faded out pretty badly and there are a thousand little ripples in the surface -- and mine WAS professionally painted.
This might be a contentious point, but I'd stay away from red Gelcoat at all costs.
Most of the bits and options seem to be either universal or at least available, so if you were to buy a good basic car for $10-15K now, you could do it up however you wanted on your own timetable over the summer and still drive and enjoy it until late in the autumn.
I'd be sure to check the pans and ask lots of questions here before you make a decision -- and given the widespread and far-flung membership here, maybe the car you'll ultimately consider buying is one someone here knows about.
Related -- Tom Jones -- You're not THAT frustrated, are you?