If the Pyra did not exist, I would probably be on the pre-order for the GPD Win. All the while I would be wishing for more/better expansion and connectivity options and Linux compatibility. The two products have much in common, but they also have a lot of distinguishing features - some of which may become less so through time.
I prefer the Pyra for (in no particular order): Linux Debian, lots of ports, full sized SD slots, mobile connectivity, pocketability, superior keyboard layout, superior analog input (nubs vs sticks), resistive touch & stylus.
I like the Win conceptually for it's X86 Cherry Trail processor and may some day buy one for that fact IF someone gets Debian installing and running smoothly on it. If it's restricted to Windows then I simply don't have a use for it. Beyond that I don't see anything that it has over the Pyra.
Pyra costs more but does more, so I see expense as a wash between the two.
I know that conceptually it's a community anthema, but my hypothetical ideal device is still a Pyra in every way but one - I'd still rather have the X86 SoC. I know there have been a lot of us asking/longing/wishing for a subsequent X86 SoC board to be released at some post-production-success point in the mid to far future. I also understand that it, "isn't that simple," but knowing that doesn't make it less appealing. All else the same, rational or not, I would perceive an X86 Pyra as, "better," than an ARM Pyra, even though I don't do Windows.
My order is in and I'm looking forward to getting a Pyra. So far I'm just not really seeing much use for a Win in it's current form.
ED should sell both - they're different audiences. Yes there is some overap, but there is overlap with phone users, handheld console users, laptop users, etc. As the convergence device, overlap to other devices and needs should be expected.