GWX is the only reason I stuck with SH3 this year. I did check a few games, but I just went for the realism. GWX is just too much against SH5. That, and SH5 won't probably run on my laptop.
To the OS part - I believe that Microsoft (and other companies) did learn something about older program compatibility in the past years, so I think that whatever can be easily run on the current OS, will run on the next one too (maybe with little tweaks). For now, the SH3 community is strong enough to patch the game to the next OS anyway, if it didn't support it.
A subsim capable of surpassing SH3 would have to be very VERY good. And still, it would be a hardware-punishing game, so the users of older machines/smaller laptops will still stuck to SH3.
Microsoft did a baaad thing with the XP->Vista transition, many games do not work since that time... I hope they did learn something.
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