Ah, that explains why 95 and ME were better than 98 and 2000.😛
Even if you break it down properly, it still doesn't entirely hold true:
95 - great
98 - great (Second Editions can be ignored here) (95 v1.1)
ME - ugh
XP - eh... not at first, but grew very popular for various reasons (2000 v1.1)
Vista - had major issues at first, for some, but turned out to be great
7 - amazing (Vista v1.1)
8 - opinions vary (Vista v1.2/ 7 v1.1)
2000 (Windows NT 5.0) was an Enterprise-only release in the eyes of most. At that time, and at the time of ME, the NT kernel still wasn't in the Consumer versions. They thankfully addressed this, the split-track OS versions disappeared, NT became the standard, and hell.. now the NT kernel is in literally all Windows releases. The UI approach they've done this with offends some, but they're actually taking the best possible path forward.
What they screwed up was the inability for users to configure the UI in Win8. There should be a "backup" option, similar to, say, Gnome 3 Shell offering a Gnome Classic fallback. Give users the option for a Windows Classic fallback, and all will be good.
Especially once the promo price drops, Win8 adoption for existing installations will drop - but there's a chance a Classic Mode option may save face a little.
If they introduce a Classic Mode, they can get rid of it in a release or two and not suffer any serious fallout with customers.
But right now, Enterprise adoption will obviously be very low since it's the new OS. But since IT Admins may also very much hate the new interface, and may see the enterprise users as also loathing it, when Win8 is late in life it may still suffer low enterprise adoption.
Considering the past three releases have been point versions of the kernel, I am actually kind of interested to see what will happen with Windows 9, if that's the next release. Perhaps the next one will be Windows 8 SE?
If the next one is NT v6.3 (i.e. Vista is 6.0, Win7 is 6.1, Win8 is 6.2), it may entirely depend on the UI approach or marketing, or be determined by success of Windows on other devices (Windows RT, Win8 on tablets, etc) if MS chooses to go the stubborn route and try to force adaptation to their new ideas.
At this point, Windows 8 is actually quite a bit like Windows XP (not at all like Windows ME). Many hated the new interface design (but a Classic theme was available), and many hated how different settings got shuffled around and changed up. On the consumer side, it was very different - but I don't think much changed between Windows 2000 and XP in terms of where settings were. XP was essentially a tweaked and improved Windows 2000, with a new but godawful dress. Windows 8 is basically a tweaked and improved Windows 7, with a new and shocking dress that, like fashion, may be here to stay, or may be shot down.
XP performed terribly during initial sales metrics, but ended up being a beast in the market. I can't say I expect that for Windows 8, since, as opposed to XP's timeframe, the NT kernel has been around the block for a few laps. I like it, but ultimately it's a minor improvement (in the grand scheme of things) over Windows 7.
If the next version of Windows is NT 7.0, I'd say we can expect lackluster sales for that. There will be driver/kernel issues, like Vista, so early adopters will have a bit of pain.
Seeing as they just got Windows NT 6.2 to a few devices that were never privy to the party, including support for an entirely different CPU instruction set, I would be extremely shocked to see NT 7.0 up next. Windows 9 being NT 6.3 makes a fair bit of sense, and provides a much better chance to recoup any negative views attached to Windows thanks to Windows 8. If they follow up Windows 8 with what would appear to be another rehash of the Windows Vista pains (early adoption driver pains caused all the problems in the end - I loved Vista once I had stable drivers), Microsoft would probably be in for some trouble. Two critically-despised OS releases in a row? That would be a bad time to be a stock holder.
NT 6.3 would probably be the best time to start up a decent yearly-upgrade program if they do go ahead with the Windows Blue project. Get two or three cycles of that with cheap prices, and probably have a major release of NT 7.0 attached to a higher price.
But hell, I still don't know if Microsoft will really end up trying that route - I'm having a hard time imagining how that will integrate with the enterprise world.