I'm feeling kind of stupid here... Can someone help me figure out why my clutch won't disengage?

Well, Tom and everyone else - I have to say, my heart is swelling seeing all the cool kids showing up on my thread to cheer me on. Thank you guys. I hope I didn't come across too poorly; I was a little ruffled, feeling like I was being called out personally by the Mayor when I swear, I'm not trying to cause any trouble, honest.

Anyhoo, I did take it apart again and, with all the clutch plates removed, bike in 1st, it does roll. So the problem lies in there somewhere.

I figured I may as well button it back up and see if somehow it would magically work. Interestingly as I was torquing the bolts/springs on the pressure plate, toward the end on one of the bolts I got a little "clank" where it felt like ..something.. had been caught up on ..something.. (nothing obvious) and then got to a point where it pushed past the obstruction and popped into place, which then left me a little more slack to tighten up in the rest of the bolts. No idea what that was. I'm pretty sure it wasn't any kind of herring. I continued on, got the cover replaced and hooked up the cable again and it was quite a bit easier this time. Not as loose as I expected, but easier.

And, importantly, the bike now rolls - just barely - with the clutch lever pulled in. There is a whole lot of drag however. Way more than I ever remember there being.

So, should I run it? Do you guys think this gasket will survive? It was new only a couple weeks ago.

Pics below in case anyone can spot anything obvious. The lower one is the steel plates. It was a little tough to show but they seem very flat. Stacked like this no light shows through between them.

Thanks again everyone. I appreciate you all!

@Gloopis,
It sounds like you may have it sorted; I hope so.

A couple of things. The pressure plate is a very simple mechanism. It's sorta like lifting a pot lid off of a pot. It provides clamping force so that the steels and fibers can transmit torque. The five springs, combined, create a clamping force of about 225 pounds. There are three levers involved in operating the clutch; the one down at the clutch rod, which is about 10mm long, the one the ball-end of the cable attaches to which is about 25mm long, and the clutch lever at the handlebar, which has a PIDOOMA mechanical advantage of 4:1. All told, then, the mechanical advantage in the system is 10:1. The clutch pull should be about 25 pounds or so. (All you guys, keep me honest here. I didn't measure anything, I'm just winging this. If I'm way out of bed, tell me.)

If the clutch pull is more than that, then there is likely an issue down in the pressure plate with the springs, because they are what's holding it back. It's not likely to be anything with the release lever, or its bearing, or with the cable because it is new, or with the hand lever because that would be obviously stuck.

The clutch plates do not really move. They just get pressure released from them. That's why wet multi-plate clutches are pretty draggy. Cold oil is quite viscous and the plates are not being pulled apart to break that viscous coupling. What you're seeing may be quite normal and you're now noticing it because you're looking at it. It is possible for steels to hang up on the hub or for fibers to hang up on the basket, but that is an assembly problem. It might be what you experienced in your second reassembly, that popping. And, if they were jammed, that would screw up the release lever's position just a bit because it might not be able to find the groove in the release rod, and that would make it hard to get the cable on. This is still a bit of a mystery to me, as the rod should have slid into the transmission's input shaft sufficiently for the lever to grab it, but then the clutch action should have been loose once or twice, and then the plates should have slid into place. Meh. Brain lock.

But anyway, I do hope that it works out on your test ride. A tip: when you start the bike up, start it in neutral. Pull the hand lever in and blip the throttle a couple of times. That will break the viscous coupling that causes the transmission to clunk hard into first gear. Then, with the bike in first gear, if it doesn't want to creep forward your clutch is releasing properly.