Max,
Thanks so much for the reply to my long-windedness. I definitely remember the whole Woods vs. Rush thing, as I feel like it's become sort of the poster-child for artists who deal with intellectual property in their work.
In the end, you're right, the First Amendment would allow me to jump some of those hurdles, but I feel like the litigious nature of that beast could create a heap of trouble for my lawyer fees.
Actually, in speaking with my lawyer a few years back, he had talked to me about some of those "transformative elements", and much to my surprise (and chagrin) bringing someone/something to life with color was NOT one of them. If that doesn't work, then I don't know what would!!
If you don't mind me asking, has your wife ever run into issues like this? Or does she just do originals? Maybe I should get in touch with some of those guys like Holland and Stark, as I am most curious to see how other artists get around these legal issues. Also, I know for sure that they're plenty of people out there doing paintings/drawings of famous people and using them for commercial purposes (though I suppose they are able to fly under the radar).