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I repeated the Ifrit Hard mode fight so many times that I can't recall how many it was. A few of them I did for weapons, but once I got those weapons, I kept doing the fight for two reasons:

1) Because it was FUN
2) I like showing off on PLD >.>

But the point was, no matter how much people raged, the Ifrit fight was genuinely fun. Sure, I've been in my fair share of wipes, been killed by my share of eruptions and paid my share of repair fees to crafters (You're welcome Rabanastre/Durandal ~.~), but it was, 90% of the time, a fun experience. The 10% of NOT enjoying myself wasn't caused by repeating the content, it was caused by players with poor attitudes.

Repeating content does not equal "Not fun". In fact, because I repeated it so much, I became a fracking awesome tank at it. I'm not trying to be arrogant, but a lot of skill comes with experience, and because I experienced it often enough to develop good skills with it, it made it that much easier/fun for the people who hadn't done it as much or were just getting started.

Not all repeat content is good, not all of it is bad. If it's well designed, then the only thing that can make it bad is other players.