I will foolishly compare the Pocket, Pyra, and Win, which I don't own, and maybe throw in random comments about other palmtops I own and have firsthand experience with if it is relevant.
Out of the gate, the Win is a lose for me across the board except for price. I guess I will just compare the Pocket and Pyra for everything else.
I can't remember the display resolution for each, however size does matter here, and bigger is better with many tasks, so the Pocket will probably be more useful there on the go.
The keyboard is a difficult area. At this size I expect to do a lot of thumb typing, however I would like to be able to type with my fingers if I am sitting at a desk or table. The early palmtops, such as those from HP, seem to have been ok for both, despite the small key size on the ones from HP. The way it feels to type on them is also important. I wouldn't be able to decide those without using them. That may be true for the layout as well, although I don't know if a final layout has been announced for the Pocket. It really helps to have a backlight when things aren't where I expect them (compared to a full size keyboard).
I don't know if gaming controls are all that important to me. I think I would miss them if I wanted to play certain games and they weren't there. I like trackpoints, however it makes the most sense to have them where your hands are going to be when typing. The location in the Pocket may be better than the standard location when thumb typing, and you have to move away from the keyboard to use the mouse with the Pyra.
For the old x86 vs. ARM debate, I can't say I am knowledgeable enough to have a preference based on technical advantages. x86 is the place to go if you want that massive library of software.
Pyra is the clear winner for connectivity, ports, and removable storage. It gets some bonus points for modular design and being made to allow the user to open it up. Not sure why I have all those different things linked in my mind.
Looks...they both look good to me, it just depends on what I am feeling atm. Metal is always nice, until it bends. The blockiness of the Pyra, and some of the little things, kinda give it that idgaf vibe, because it was made to throw as much stuff together as possible and be used and abused. Sleek isn't everything, so I like that. Both need less rounding imo, however that would interfere with pocketability, and probably how it feels in the hands (not that the Pandora has ever been uncomfortable for me), so I am glad I wasn't the one making that call.
I guess I still don't see either the Pocket or Pyra as hands down better. The Pyra has some things to offer that the Pocket doesn't, and the Pocket has some areas where it might end up better for me at least some of the time. If Linux isn't problematic, and I had the money to waste on it, I would probably get a Pocket. If I had both I am pretty sure I would carry the Pyra more frequently.