I picked the Rules. Mostly because the rules I prefer were better at modeling the types of characters I enjoy, and allowed me to play the type of game I enjoy.
I'm a Storyteller/Method Actor that prefers as realistic and plausible an environment as possible.
Yup, me too.
The only edition updates I did were AD&D to 3e, and 3e to 3.5e.
We tried 2nd Edition for maybe a year, but we liked the flavor of AD&D better, and after trying 2nd Edition for a while, went back to AD&D, which supported all the PC's (like my LE half-orc assassin, triple not allowed in 2e) and therefore "felt right" as being "the real thing".
We eventually upgraded to 3e -- but there were specific rules on how to update (from 2e to 3e, but close enough for AD&D), so we were able to continue the same characters, the same stories in the same world -- our version of Greyhawk that I'd been running for 5 years when we switched.
Then we upgraded to 3.5e. No sweat, easy-peasy as it was almost the same as 3e.
Then we saw 4e. Two of players, who also DM their own campaigns and who are more early adopters/tech people than I am, checked it out and said "No, this isn't compatible with our campaigns, so we don't like it." I tried playing it with a different DM who liked it, but it didn't work for me.
And even if I DID like the rules, I wouldn't have switched my campaigns to it, because conversion isn't easy/isn't supported. The recommendation to kill off your old campaign world and start over doesn't work at all for me.
So: lack of backwards compatibility/convertability of PC's to the new rules, and lack of backwards compatibility for the setting. The rules need to Greyhawk/AD&D friendly, or there's no point to them for me.
Which means our next upgrade, if we ever do it, is most likely to Pathfinder, not 4e, because of compatibility.