Yes, we'd all like Jimmy to sell individual live concert CD's. But with his history of barely changing up the setlist I'm not sure how profitable it would be beyond those fans who attended the concert.
My husband bought 2 concerts off the Phish website that he recently atteneded (the back to back shows at Alpine in July). And each show was completely different. Not one song was the same.
Same could be said about Pearl Jam. My sister attended the back to back PJ shows in June (She was on a Buffett and Pearl Jam bender: PJ Sunday, Jimmy Tues, and PJ Wed and Thursday). The PJ shows were completely different and she ended up buying CD's of each show.
Yes, some parrotheads may want to buy this show or that show for that one rare song they love live. But overall Jimmy would be putting out 20 some CD's that are roughly the same. Groups like Phish and Pearl Jam (who never have the same setlist twice, and even rarely play the same songs twice on a tour) offer fans a multitude of concerts and songs live.
Buy singing different songs every night, Pearl Jam and Phish are offering a "different" live CD every show they play! They must be swimming in CD money
Fans could buy every CD of a tour and no two would be alike (in the case of Phish, you probably wouldn't even hear the same song twice).
Now if Jimmy would like to mix it up and offer live concert CD's, I'll be a buying customer. But if he's going to continue doing what he's doing, I'll set up my computer to record the show off RM, or heck I'll just record any other show of the tour. It's really only the banter that differentiates half of the time.
Just my 2 cents.