My thoughts are that if a game is designed right, it doesnt need to skip anything (other than the tutorial) to get going and still be fun. As in, no need to skip to high-end equipment.
Best example of this was City of Heroes, which was my favorite MMO (now shut down). The devs entire design philosophy was that idea of "fun right from level 1, wether solo or grouping", and they made sure this was the case. None of this "only the endgame is fun" business. In fact, the game had hardly any raiding whatsoever. The devs decided that rather than go the raiding route (meaning that tons and TONS of dev time has to be focused on JUST that) they just gave everything equal attention. The game simply had no boring points, and the combat system itself was fun... your abilities worked nothing like they do in a "traditional" MMO like WoW, and if you simply tried to do the same chains over and over, you'd be really dead really fast. Had to actually think. And that's against NORMAL foes (and a typical encounter, for solo players, was around 6-7 enemies at once, each having different traits)... it got even more complicated when dealing with bosses (of which there were a great many at all levels, you'd always fight one at the end of a mission, and this included solo missions). Basically, they made sure that the absolute core of the gameplay was just constantly entertaining... so that it didnt matter what level you were or how far you'd gone, it was still fun.
With WoW though, it's just a dull (and easy) slog until you hit the "real" stuff, which has always just seemed stupid to me. What's the point of bothering? So much time lost. So I've never seen the point of choosing WoW over games that do it in the "fun all the time" way. It's like choosing moldy bread over a candy bar or something. Just doesnt make sense to me.