You can play a newbie friendly, up-tempo, fairly recognizable set while still playing a cohesive setlist that leaves the more jaded fans smiling.

Do they think Show Of Life and Alaska are actively grabbing non-Phish fans and converting them simply because their fans hate those songs?

IMO they played the furthest thing from a crowd pleasing set as was possibly imaginable without swinging far in the opposite direction and playing a 45 minute Bowie with secret language, silent jams and a 15 minute rotation jam tacked on instead of the ending.

Having the supposed crescendo of the show stymied by things like Alaska, Show Of Life seeemed so bad after them putting together a relatively awesome set of well played classics, with a few bones thrown in (Relatively atypical Chalkdust, Hydrogen fakeout between the Tweezer peak and Free, Shafty)

The repeats aren't a big deal, but the Hood denial and those two major blows to second set cohesion seemed like it at the time.
In retrospect.. It's Phish! They don't really give two shits if they end a show like the first night of Superball and everyone's acid goes bad because the band can't decide if they want to mellow or ragey. IMO everything after that gorgeous Simple jam was 100x the abortion that the end of Bonnaroo was. If it wasn't for the repeats putting so many people on edge, I'm guessing it would have been received much better than it was.

Now, to go full-blown contrarian.

This festival wouldn't exist without Phish. The whole festival scene wouldn't exist without Phish. It'd be a bunch of Dead cover bands and white reggae bands eating mushrooms in the woods of Connecticut until eternity. You wouldn't get these modern amalgamations of everything going on in the various caverns of underground music throughout the country and beyond.

I REALLY wanted Phish to GO LEGENDARY with this slot. I'm personally a fan of the improv first and foremost, but really any combination of being as Phish as possible would have cemented their legacy as the kings of the "scene". Phish is known for their unpredictability, I don't think that Bonnaroo books Phish and then hopes that they dumb it down. While I'd consider a show a success on it's own terms, I keep thinking how nice it would be if Phish would put their stamp on this festival's main stage, or even their own festival's main stage. The bands that walk away from Bonnaroo with the most new fans are the ones that let it all hang out and be as THEM as possible. Radiohead spiraling into psychedelic dystopian madness convinces a few thousand hippies that they aren't an "emo band" every time they hit these kind of stages. Because they aren't playing it safe. They're surveying this landscape of drugged out wahoos and saying "Let's blow these motherfuckers minds tonight" instead of "Lizards is a Gamehenge song, I don't think the crowd could go bananas during the most explosive piano jam of the entire weekend without understanding and grasping the full mythology of Rutherford the Brave"

Phish. Next Year. I don't care if you play my 10 least favorite songs to do it, but reach for greatness on the big stage. You owe it to all the people who aren't yet fans.