Quote Originally Posted by Reimmi View Post
Also it's squares fault that there's even a difficulty spike like that in DT because they never challenged players in the leveling process
This one here is a big one. Whenever Square introduced some sort of gate in the game, people complained about it (see - Steps of Faith). Relenting to that of course meant that any incentive to get better through the MSQ just poofed away.

That being said, the discussion about difficulty of content kinda breaks apart from what OP initially brought to light - namely that with how ilevel scales, fights lose part of their appeal. No sense of danger, and bosses die before they can do the cool thing. (I recently skipped over the DPS race in M4N and that was... off putting to say the least.)
Of course, becoming stronger is a core central theme of any MMORPG. However, the level sync system works against that notion (which is not a bad thing, mind you). Level synching could benefit from a rework at this point in time though.