This podcast reminds of every conversation about phish that I have had with all my friends, it is very hard to persuade people to love phish or even like them. Anyway, I myself have been listening to Phish since i was about 14(2006), it was after they had already split up and i live in texas so i have never seen them live(i did have tickets to ACL of 2010 but couldn't make it)... also i have never used drugs. However, I have listened to Everything they have published and alot of audience recordings. The way i started listening to phish was through the Madison Square garden new years eve 95' cd i think it was the combination of Gamehenge story telling and Who covers that hooked me. i felt it important to state that before what i type this.
I do have some suggestions for what you should play for someone who is just beginning to listen to phish because like you said people do scare easily
-- I would show them--- Bouncing Around the Room, lawn boy, Rift, limb by limb, NiCu, Brian and Robert, the connection, Army of one, Farmhouse, joy-- The studio recordings of these songs are not threatening to people and they adapt quickly to these i have learned
then you slip in some heavier, live songs like --Character Zero, wilson, foam, axila, cavern, wolfmans brother
you can transition to other live songs like--- Weekapaug groove, Maze, Tweezer, Golgi Apparatus, Slave to the Traffic light
if you haven't already lost them by now you can do the deep cuts like--- YEM, guyute, Stash, David Bowie, Run Like an Antelope, Harry hood
And then you can show them Harpua!!
covers in my opinion don't really count they're like an inside joke for phish fans but all i can do is suggest the ones i think are the best..... you played the talking heads i would have gone with the Great Curve vol. 15, My personal favorite Don't pass me by from Vol. 13, audio not so great but Cover of the Rolling Stone 02/14/03
i hope this helps, i really enjoyed the podcast and look forward to the next one.