I have had windows/mass production umpc's like the GPD Win in the past and was underwhelmed each time.
The Pandora had been wonderful, so I'm going to stick with the Pyra rather than tryout something brand new
This is kinda how I feel. I was never into UMPCs, but loved Palmtops from the first time I saw one (probably a movie about time traviling killer robots). When I bought one I went with one that had MS-DOS instead of Windows, even though I could throw Linux on the Windows ones, because it fit my intended use better (actually, one of my crazy plans, and the thing that motivated me the most to buy it, configuring routers, worked out of the box).
If I was more of a Windows user/gamer I would probably be more interested in the GPD Win. Pyra is better for me because it is about choices, comes with Debian (I may not get around to throwing something else on very quickly, however I know what to expect with Debian, and am familiar with Linux in general), it comes from a smaller company run by a man that interacts directly with the community, the community is what will help make the Pyra a success, and I view it as a next generation of the Pandora, which I am pretty pleased with. There are a bunch of other things the Pyra will have that the Win will not, and I want those (backlit keyboard with a layout that makes sense to me, 4G, external indicator LEDs, multiple SD cards and ways to boot it).
An additional thing to consider is if you will be using mostly x86 software. While it may be possible to run some of this on the Pyra, if this is something you need and want it straight out of the box you will probably be better off with an actual x86 CPU.
I understand the interest in 3DS and PS2 emulation, as I am with you on that. For me, right now, 3DS isn't all that important, and for the few games that I would like to play I will just use a 3DS. PS2 is about as recent as my major console interests go for emulation, however I will be happy enough with what is already planned (DREAMCAST! also I have so many older games to play I am probably set for life). If you really want 3DS and and PS2 games, and you know one device you are interested in WILL let you play them, while the other MIGHT, go with the one you know will have it...unless there are other factors that are more important.
Again, if you want Windows software out of the box, go with the thing that ships with Windows. If you are fine using something else that can offer you the same capabilities, or if you are ok messing around to maybe get the Windows software to work, keep the Pyra in mind. I personally enjoy working to get things running, and it helps me learn.
ED mentioned the price above, so I have nothing to add.
Ok, in addition to what I said a minute ago, only you can decide which is right for you, and both may be fine. The Pandora is weak in a few areas for me, and the Pyra seems to fix all of those for me. The Pandora was sufficient for some of my school assignments, however for many of those where it wasn't good enough neither the Pyra or the Win will be a much better choice over the other (many of my classes have been highly technical, so software is usually available for windows and Linux, however when it came to other assignments, such as running 2 or 3 VMs, even the classroom computers weren't sufficient many times, so while an x86 Windows palmtop may seem better it wouldn't work for that stuff).
Pentesting, as with many things, is really about your personal knowledge. You can have the best rig in the world, but if you don't know what you are doing it is useless for that. I would guess x86 might have more tools available, however it is highly likely I am wrong. On the other hand, even a cheap old Android device may be sufficient for your pentesting, and I did a demonstration of this to show how you can have a cheap and disposable pentesting setup that wouldn't raise too many red flags with observers (note: this was assuming you are attacking via wifi). Really, I think either the Pyra or Win will be fine for pentesting. Depending on the situation I would think a laptop or smartphone might be a better choice, plus there are many other things to consider.
Emulation and gaming...well, both offer you plenty. GPD has made some decisions that seem utterly foolish to me (disabling most of the gaming controls when using one of the sticks as a mouse??? what about all the games that use a mouse? Maybe they expect you to use the keyboard with those games, however the keyboard itself has major problems, but those will supposedly be fixed soon). There are really a few things to look at here. When it comes to emulation in general I still think the Pyra has the upperhand when it comes to controls, however the Win probably has greater potential for emulators. If you want the big name Windows only releases, Win is probably a better choice, however both are somewhat limited. The biggest benefit here is the modularity of the Pyra. We don't know what will happen, but anyone can release a new CPU board that could end up making Pyra a better Windows gaming option than Win. The Pyra may never get a new CPU board, but even ED says he wants to release one. Also, consider nubs vs sticks, and cross d-pad vs the circular one. They each have their own streangths and weaknesses, but many seem to prefer what the Pyra will offer, and, despite being a Nintendo fan since the NES, I think I agree with them. Oh, I completely forgot, Pyra just seems better with location of all L and R buttons (2 are on the nubs, where they belong) plus we have 6 face buttons, even if the new ones aren't in optimal places...I mean, at least they are there, so you can use emulators and games where you need those (think N64).
Learning: Pyra.
For programming you should ask those with more experience than me, however that was a major consideration during the keyboard wars, I mean discussions, for the Pyra.
"Daily stuff" doesn't really tell me what you are doing. My daily stuff is different than that of someone that uses tons of social media, or someone that only wants to watch porn or whatever. The Pyra looks like the best option for me based on current info about both devices.
For both programming and many regular computer tasks a decent keyboard is very important to some of us. At the very least you need a sane layout. The Pyra layout was discussed to death, back to life, back to death, then burned, and eventually we ended up with a bunch of ideas that were incorporated into the layout choices we voted on that were only possible because so many of us threw out our ideas and how we plan to use it. GPD didn't seem to give any thought to their layout for a long time, just going with something that looked "right". Sure, their space bar is centered, but did they consider all the different languages, what different people want to do, how different people will hold, or not hold, the device while typing? Highly doubt it.
The general look and feel of the Pyra keyboard seems better to me. The backlight will really help me. I don't know what GPD is planning to do with the caps, however the keyboard I am typing this on is similar to that style and about half of my keys are missing paint, with some so bad there is nothing showing what the key is (e and t, with r, d, f and shift almost all gone). This is because I sometimes push with my thumbnails, and I type a lot. The Pyra keycaps should prevent markings from being lost since it is a thick piece of clear plastic over it. The feel of pushing the keys is also important, and ED, as both a Pandora user and by listening to feedback of other Pandora users when making the Pyra, knows what works best. We will really need to wait and see which is better when it comes to all this, however my money is on the Pyra.
Finally done with this post. Now I can go read more of the discussion and reply to others.
