Your gaming comment struck me. I had a couple of games that I owned legally for which the copy protection scheme was incredibly annoying. Reading codes printed in black ink on really dark paper, having to look up word #9 of paragraph 25 on page 15, etc. Those were the games I had very little trouble in justifying a hex editor to switch the answers to empty or some common word just so I wouldn't be constantly trying to find the manual.
I didn't pirate the games nor give an "unlocked" copy to anyone else, but the copy protection was definitely anti-consumer in the sense of guilty until proven innocent. I know that there are now less intrusive forms of copy-protection, but they still go overboard at times even to the point of installing what's just about a rootkit. (And then seem to wonder why people look for cracked software or "NoCD" patches.)
I'd also agree that MS' licensing just seems to grow more confusing every time they release a new version. I don't really like their "Genuine Advantage" or "Software Assurance" programs too much. Sadly, nobody ever really indicates whose advantage when they name these programs. I'm pretty sure it's not MS' customers.
As for the licensing, it would be nice to have an easy way to keep track of it for corporate purposes. Computer X has been retired, all of its licenses are now available for use elsewhere. Stop trying to tie a particular copy to a PC and then not allow people to upgrade their own machines or tinker with them. Don't require Corporate servers to validate PCs on a regular basis - poll them perhaps, but not checking in to see if they're still licensed. Can't imagine the outcry if some odd bug worked in that invalidated all of a major corporations Vista licenses. Make it easier on the customer, guarantee a minimum number of upgrades if you're going to pay for SA, don't use audits as a threat to make people buy into SA or a similar program.
Sadly, it appears that Apple is now pursuing something similar to WGA for OSX. I guess they didn't really hear how well it was received by MS users. (Either that or they figure that Mac users won't care.