Nicely written and fun to read.

A couple of related points:

1. It was obvious to anyone listening that Phish was completely falling apart in 2004. So then the thing is to go back and listen for clues as to when everything started coming unglued. To my ear personally it's summer of 1999: The fifth year in a row of playing the same shed circuit, the ambient strain started to make its way into the music, visibly fucked up on stage (Oswego Piper). Big cypress was the knockout blow. Other people go even further back: some pointing to 1997 as the time they stopped practicing, started to party, etc.
Here's a truism about life: Nothing lasts. Nothing. Phish spent so much time getting good and then being great it HAD to hit a peak. So I'm not sure that you can blame drug use or lack of motivation because I would contend that these are, after all, four human beings and human beings cannot maintain that level of dedication and focus indefinitely and if they try to then they will inevitably start to get fucked up to blow off the emotional strain, fan expectations, stress on their relationships, travel, etc., and eventually self-destruct, which, coincidentally enough, is exactly what happened. Point: this point in the arc of their career was more or less inevitable. The self-immolation is the cost of that level of greatness. At some point, there is nowhere to go but down.
2. And this is all opinion and I salute you for taking a preemptive stab at an argument for 95, but December 1997 is without a doubt the best month ever. A few years ago, just for kicks, I listened to December 1995 date for date all the way through. It was fucking exhausting man. There are some truly stellar, absolutely career-defining moments, but they are all very much of a type, and by about halfway through December, it sounds as though they had gotten kind of tired of the whole thing. I honestly was getting migraines halfway through that month just listening to it.

Of course, stepping back, it's fun to identify the peaks, and I used to love to roll up my sleeves and dig in for a good comparison of those peaks, but like, what's the point anymore? They were both great months. Let's enjoy them all, including the tours you mentioned above, which was spot on in its assessment.

Trey windmills all around, boys.