I kinda think SE made the right decision. Save the harder stuff for later when the game is more developed. Now is a time for motivation on a wide scale, and this way of presenting the classic gear is a perfect way to introduce the new job system to everyone. Making it too hard to obtain just shuts too many people out of a particularly exciting bit of new content before the re-release at 2.0, and we get to look cool while testing and determining pros and cons to the system. After 2.0, I'm sure there will be many chances for SE to provide challenging ways to upgrade the classic gear, or perhaps introduce "relic" versions like FFXI did with Dynamis and make them rediculously tedious to obtain.

I do agree that challenge breeds inspiration and garners a feeling of accomplishment upon completion, but that should be saved for something truely powerful, not just some Job quest and it's rite of passage... I believe the classic gear is just a taste of what's to come, and hopefully will motivate more people into participating in that crazy difficult endgame content that will start poppin' off when the game truly kicks off. Of course me personally, if I'm to be tested, I want an actual challenge with a definite reward. I don't need another drop-rate induced time-sink like FFXI... but that's another topic altogether.