They could conceivably have close to the same gear as the best players in the game, within a time frame in which it still means something and hasn't been completely invalidated by the next content patch, thus the rewards have more instrinsic value and the likelihood of someone embarking upon that journey (and staying on it) is higher. That the wider community recognises the content is much easier in terms of skill I think has less impact than you imagine, because a) within the context of the game world the rewards still have the same level of prestige and gameplay impact and b) to the bad player it will still have felt like a sizeable challenge, in the same sense that the satisfaction of reaching level 60 is not going to be diminished by the fact that the world first 60 was done in 3-4 days.
Retail don't forget not only constantly reminds people they lack skill, it also reminds them they are too slow. Introductions like Ahead of the Curve means that even dogged persistence can't compensate for the bad player, and such reminders of their failings can even become requirements to get into raids, rubbing further salt into the wounds.