Well, I think the goal here is not to make things more difficult for people. But unless we REALLY want to limit our game and system choices to certain well-traveled paths, emulation does actually make participation easier, because people don't have to go out hunting for hardware and games that may be damn near impossible to find.
I am all for random selection, though quirky and less known games definitely need some loving first, especially some of those hidden gems on Racketboy's lists.
I voted semi-chronological. I don't like random because it might make things harder for us when we "go back", like playing an 8 bit game after a 16 bit one. If you play Chrono Trigger after Asteroids it'll look like next-gen, but if you play it after Jet Set Radio it won't be so impressive.
Yeah semi-chronological will be better. I think we could make this by genre, and go through the most important titles throughout the years, and the selection of the titles could be by voting.