Fun idea for a series and I think you should keep it going.
I suggest that you stop skipping around with the songs, just let a few songs evolve and blossom in their entirety. Right now it is like jumping around in a movie or only showing a part of a painting and expecting someone to appreciate it (or even more unlikely) like it. Maybe even edit out the music on the podcast then just tape the commentary after you all have listened (in a less stuffy location than a soundroom ffs -- find a nice couch!). You can link the phish fans to what you played so they can follow along if you like (and spare the non-phish fans so they don't have to endure it).
For example, Slave to the Traffic Light is all about the gradual buildup and textual layers ultimately exploding in glowing confetti -- that can take 10 minutes or it can take 30 minutes depending on the alignment of the stars.. taking any part of it out of context is depriving the listener of the full phish pan-sensual experience.
In the end, passion is contagious and open-minded people will explore the things that you love to see where all this positive energy is coming from inside you. Even my mom bought a few albums when she wanted to find out what was so great about this band that had me running all over the country in 2009 (30 shows in 10 states I think). She found it noisy (liked the ballads though) but "got" the whole music of the moment improv thing and in her own way saw the magic that these four musicians create when they take the stage together.
