My 2 cents.
I reckon it will be a good thing if OS4.1 was able to be emulated on WinUAE. I always worry that when my (now 10 year old) hardware eventually goes all time investment in OS4.x goes out the window, so I tend to write for 68k because I know I will be able to keep using it in future. If there was OS4.1 classic emulation I would be more inclined to write things for it as I know my time investment is not gone when the machine fails.
I think the emulation will happen on WinUAE because even if Toni doesn't have interest in that bit, I'm sure someone else with those skills will.
Like many, I would love to buy an X1000 but it just costs too much for me to afford (and I really tried to kid myself last month too!!!).
My personal opinion is that 4.1 should be the last version to work on classic anyway and 4.2 should break that tie, working on the future (hopefully) more affordable machines. Since 4.1 was current for so long, it doesn't hurt to target that version for a while, even using emulation, anyway.
If WinUAE supported Classic 4.1 I'd buy a copy for sure.
Finally, Hyperion could not be expected to write drivers for software that they don't support. It is up to the emulation to be right and/or specific drivers to be written for the emulation by interested parties. If Hyperion happens to become one of those interested parties, all the better.
Phew! I think that's enough