First of all, this show is such a great idea on a few levels. Obviously Scott and Harris have great chemistry together and it's always fun to hear them banter. Also, great SEO putting up a show with Phish in the title. That should put some butts in seats.
My first show was on 7/23/97 in Atlanta (still the best Ghost of all time) and I've seen 20 shows since then. My last show was in 2003. I've really grown apart from Phish but I'll always consider some of those shows to be among the best experiences of my life. Sometimes I think I may still be at Lemonwheel actually.
Anyway, I think Harris' picks were kind of spotty. I know he was picking out some of his personal favorite songs, the songs that mean the most to him, but I don't think that's the way to go here. The song that got my friends into Phish back in 1996 was Bouncing Around the Room. I wouldn't recommend that as an entry point for Scott but my point is that the song that gets somebody into Phish is not usually a "heavy-hitter." (Of course the song that got me was the Harry Hood from A Live One.) The problem is the lyrics and the singing. I've always said, even when I was a fanatic, that Phish should just stop singing. Or hire a lead singer.
Here's what I suggest: I know Harris said they couldn't just play one of the deep live cuts all the way through. But why not? If it's for legal reasons, that's one thing. But I think it would be interesting if you let YEM or Harry Hood or whatever play in its entirety and kept the commentary going on top of it. Kind of a crunchy MST3K.