A little late to the party, but as a reformed Phish evangelist, I'm quite enjoying this. Harris, you're doing a great job, keep it up.
I'm glad the next show will focus on longer cuts, but remember that a deep heavy jam is probably TOO much. I'd look to the San Francisco show from this past summer for tracks. It's a larger festival show, so it's more accessible to newcomers, and it also rages. A good one-two punch would be Funky Bitch and Moma Dance. The first is a cover, but it's a good jam, and can help Scott get comfortable with how the guys sound together. Plus, the lyrics aren't by Tom, and Trey isn't singing. And, well, Moma is Moma and if you don't like that song then you just hate music. Scott dug on the studio version, let's get him into the jam.
Scott, I really think you need to open up a bit more. Your own comedy is so bizarre and goofy and at times inaccessible, I find it a little surprising you're so quick to dismiss a Phish track citing similar traits. Another criticism you've repeated is that they stay "safe" with the silliness and the "happy" chord, but keep in mind this is the foundation of what's often a very heavy and intricate piece of music. You need it to stay grounded, and to have a good place to land. It's not going to "wow" you in 90 second chunks, or if you don't let yourself be drawn into it.
I get the feeling you're waiting for Phish to prove themselves to you, but I think that arms-crossed approach is counter-productive. Instead, try to open your mind to see what it is they're attempting and judge it on those merits, and see the stuff you dismiss as part of that greater whole. Phish is the best at doing what it is that they do. The lyrics aren't high art, but they're not intended to be. Your own comedy is often strange and full of fun word association. Yelling "freeze her with a tweezer" is just a fun thing to sing along with at a show, and the words themselves get your face to smile, which then opens your body to be receptive. It's silly, but it works.
Anyway, keep up the fun podcasts! I hope it takes you a dozen episodes to fully appreciate them!