Originally Posted by Prinsesa
Echoing this sentiment heavily. I've healed through Bloodboil and Teron despite my Holy set not having a single piece of gear past Karazhan. Between Craftable, Badge and PvP gear, it's not terribly difficult to catch up with progression.
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Not to take away from your point, but paladins seem to be especially able to perform well as undergeared healers. This is entirely anecdotal, but I've seen it mentioned a number of times in different places. Holy paladins in my guild have also mentioned that they don't feel like they're getting much of an upgrade going from T4 to T5 to T6.
Whatever the case, from the point of view of a reroll guild it shouldn't be hard to find your comfort level; you just keep pushing progression as hard as you can until you run into a gear-check wall.