However, the ability to arrive at "similarly situated characters" is not distributed in an equitable manner, and that grossly tilts the playing field. For example, WoW trades advancement for time. If you've got 720 hours to kill and spent them in the same calendar years as I did, you were going to end up with a level 60 character and a fair amount of gear (with differences depending on your WoW skill, guild, etc, but negligible compared to the differences between a lvl 1 and lvl 60 character).
Maybe skills would let you lead a raiding guild taking down what was then "top content", maybe they would not. But if you didn't have 720 hours free, perhaps because you had to work three jobs to keep your children fed, then you weren't going to be leading that raid, regardless of your charming personality or skill with stance dance.
(Speaking of stance dance, I have a few years of practice of flipping between Academic Liberal Or At Least Educated By Them and Republican Somewhere To The Right of Atilla The Hun. Sometimes in the same conversation.)
Heroic modes are a different story though.
The Dungeon Finder (with which you can find random parties for random instances) also employs a gear filter, albeit less outrageous than human players.
It's interesting as a near-pure meritocracy too. A 15-year old kid might be calling the shots for 24 other people twice his age if he's got the experience and skills to lead.
It becomes a treadmill pretty quickly though.