I recently fantasized about doing this. I think jumping around would be a good idea to vary the experience. My idea was to do it for charity and seek multiple donors pledging an amount per show. Two shows a day would still take around 5 years.

Other idea is to do all versions of a specific song. How about the ultimate Me and My Uncle Marathon!

Second thought, Dark Star or Playin might be more interesting.

Personally I would go with a ballad, either Stella Blue or Black Peter.

There should be a t shirt for that!

I like the idea of doing it in chronological order. It drags on and will take a long long time but I've got time to spare and I don't think I'm dying anytime soon. I also like doing it chronologically because you can follow the history of the band with each year/month/show.
Like right now I'm at the point where Lenny Hart becomes manager....