It's amazing what a little extra free time allows [(heh) I'm not having to write content for class as it's summer vacation!]. In any case, I can now say that it is possible to hook Skype to Asterisk. No thanks to the worst documentation that I've seen, this side of the millenium, I now have a demo Skype-to-Asterisk bridge running. Next on the agenda, find out if DTMF works well enough to control Asterisk, move it to a production machine, and post my notes.
For now, let me say that there are a number of drawbacks which some may be able to live with, some not. For a $20 license, I don't consider it to be too bad of a product.