There are two ways to answer that question. One is to suggest that there is no difference between Microsoft and Apple’s design and implementations, and it is simply a question of prejudice.

The other is to suggest that on balance, Apple’s changes pay off positively for users while Miscrosoft’s do not. In which case they are both doing the same thing in theory, but different things in practice.

Are you arguing either of these cases?

Perhaps there have been sufficient missteps, though, that people feel they have both license and cause to second guess major changes.

Whether Win 8 itself ends up being successful or not is still an open question, of course. But I will be happy to wager that (A) there will be a major next successful version of Windows, and (B) it will look a lot more like the Win 8 Developer Preview than it does like Win 7.

Not that I disagree with you, but it would be fairer to include Microsoft's serious missteps like DOS 4, Windows 286, Windows ME, and Windows Vista.

Err what? All the apps still run and run natively. This not even like Apple's move to Intel. It's just the Start menu UI that's being changed. This is more like the Ribbon UI being introduced in Office 2007 replacing the traditional toolbar.

There were predictions then that companies would shift to OpenOffice because the ribbons were too jarring to users. How did that turn out?

My point was that the comparison must take into account the culture each company takes toward accommodating the needs and tastes of legacy/long-standing customers. Pulling out one example - the Ribbon in Office, which people still bitch about to this day, mind you - does very little to argue that Microsoft has a tradition of bold changes breaking existing user expectations. Such an argument would need to be much, much stronger.

I am curious regarding MS's big changes that you consider that didn't help users, Vista? Office Ribbon? Windows Phone 7?

2) Microsoft's users are likely more change-averse than Apple's.

3) Over the years, Microsoft has cultivated a reputation that is rather different from Apple's. That directly affects how the two are perceived.

Microsoft has built a reputation of maintaining a consistent and reliable platform, and bending over backwards for backward-compatibility. Why are they giving play to the avant-garde UI experimentation that, all things being equal, might drive desktop customer back to MS? I've read more than one report of people fed up with Unity or Gnome3 switching back to Win7.

To some extent, Google has a similar disconnect. Their main customer isn't the end-user, it's ad-buying businesses, and, with Android, handset and tablet vendors. Either way, it's not the end-of-the-world, but I think it's a key basis that leads to how the different products of the companies end up in terms of polish and integration.

Additionally, for better or worse, Apple's hardware cycle tends to be a lot shorter than Microsoft's-- the fact that you can't upgrade a system piecemeal pushes people onto the latest and greatest, which means it already comes supporting the software for the same, as opposed to the people still using Windows 98.

Apple products need to be beautiful. Microsoft needs to be accessible.

If Microsoft doesn't have the brand loyalty of Apple, it is foolish (for it) and annoying (to us) for it to try to leverage loyalty into a willingness to suffer now for the future.

Edit: plus, Apple has earned (or otherwise acquired) a trust level that lets it ask its users to wait for the future. I don't Microsoft has this.