I believe the way to approach issues of this kind is to look into adding some functionality to the attribute system. I would like the ability to push the configuration to an ahah handler, which would reply with some of the key items(price, image change, or additional options based on the the option chosen).

As far as how we should do this, there was some discussion before 'the crash' about performing image changes and the product attributes schema as a whole.

I am interested in taking a look at this, but I have 3-4 other items on my list first.