What amuses me in all of this is you are all assuming that the OP wanted a guide on how to gear. From what I read, the OP is asking how do you do a path of content from 2.0 to 2.4 without missing out on the challenge that was initially there when the content was released.
Quote Originally Posted by Dimitrias View Post
It sux for new players to once they hit 50 and can't experience the game like we did in the past, or is it still possible to progress naturally with endgame, from 2.0 to 2.4?

It also seems like you would get Caried through all the older content aswell, and some people would like a challenge
OP: If you are looking for the content to progress in a similar fashion and still be challenging, you should find 3 other like minded individuals. This would let you challenge each dungeon along the way in gear that is the iLvl that the dungeon was designed for. If you are relying on DF and hoping to do this solo, it is not likely that it will happen as those who have been in the game for the last year have no interest in gearing down to an instance that they have cleared time and time again.