I'm not so sure the level of detail is an indication that he's disconnected with his own company's products. The vibe I got was that he was trying to describe to the people who build this stuff what it's actually like to be an end user. I think the whole point is that they're the ones who are disconnected and completely out of touch. I seriously doubt that Bill Gates _needs_ to download and buy Movie Maker from microsoft.com like a customer would.
Even if he is the one who is totally disconnected I thought all of his points were excellent and a perfectly accurate illustration of how Windows has gone wrong. What I'm left wondering is what's been going on there the past several years. If these critiques by Gates are something new it's a real shame for Microsoft that he didn't start sooner. If his statement that it's his job to do this every day is accurate then I'd say they have even bigger problems.
He should have been able to be a lot more specific and detalied about what was going on, and not complain in generic terms "downloaded more stuff, this popup here, that thing there".
It seems that back then he was not involved at all with the development of windows. It feels like comming from somebody that just started using it, and not somebody that build it (or gave guidance on building it). And this was in 2003, so Windows XP had been out for about two years.