I've talked this over with a few folks. Ran into several issues.
First, the qualified driver thing is, I think, not that big of a deal. Raceday is the only day that you have to have drivers with a set number of rolls in a buggy to roll (as far as I can recall). So long as a driver is caped I think they should be able to roll.
When would this happen though? Exhibition heats are scratched all the time, and they should be because it would be not cool to let the alumni race and then have finals rain out. I know alumni want to come out and roll but... well... considering the competitive spirit that some of us possess I would think we would want a decent chance at rolling since I would imagine we'll be bringing all we have. To be honest I don't think rolling alumni on Raceday would be best since, again, it could endanger actual races, which would suuuuck. I would propose Homecoming weekend. Heck, we might even be able to close the roads for longer and only allow alumni to roll after, say, 8am (or whenever rolls normally end), so that students are unaffected. Plus it might be cool to have a pre-pre-Raceday to get more kids excited about buggy early in the year, or something.
What would the teams/buggies be? I would suggest we only allow older and/or retired and/or 'alumni' buggies. I would think we'd like to avoid any sort of thing where folks are using alumni races to get rolls on their raceday buggy, or something.
Finally, would it be safe? I just have this vision of Bordick in lane 1 holding Maddog with me in lane 3 holding Demani for the 'Spirit vs. PiKA mechanics' race and when the countdown hits 5 seconds we switch out for a 'Spirit vs. PiKA Pusher All-Stars' race while Sweepstakes starts freaking out. Granted, that one wouldn't be close, but, you know, maybe Jay loses a shoe or something and it's kind of tight going over the hill.