On the surface, I like your idea. I'm one of those people that loved the Triumph of the Nerds series on PBS and wish I had Pirates of Silicon Valley on DVD and absolutely love reading about pioneering computerists -- specifically those in the very late 1960's through the late 1980's. I find the people and the issues they deal with during that time far more interesting than the very earliest computer-related history.
I've had the fortune to have brief conversations with many of those people that have been the subject of my historical curiosity and I would pay a large amount of money to, instead of having a tour, have some sort of a 'vacation' where I and a very small group (at the most, ten and preferably only half that number) of interested individuals like myself could engage these individuals in luncheons or something. I'm not sure how you would draw their interest and make it worth their while (although for people like Wozniack, who are such fun and friendly guys, there might be little arm twisting, if any). Still, if there were a way to get a group of these interesting people together (perhaps a rotation of them so that they could make themselves available a few times a year each) in a nice setting with intelligent 'tourists' to discuss things with, you could probably do pretty well.
I'd consider paying perhaps $5,000 for a day and night with a group like Woz, Bill Joy, the guy who really invented MS-DOS, Linus, RMS, ESR and any number of others. Get a group of five people together every three months, charge $5,000 and you've raised $100,000/year, at least. Perhaps you could even work together with them to donate it to charities of their choosing (FSF, EFF, disease research... whatever).
I just read K5 for the articles.