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. :D)