The Dilemma Of Choosing Gear

Choosing gear used to be so simple. When you roll a new character, you start out with the crappiest of the crap. At first, it’s just a matter of picking whatever has the highest armor rating. Couldn’t be easier. Then you add in stats to consider. Would you rather have agility or intelligence? Is your character more suited to armor of the bear or of the tiger? Are you mainly PvE or PvP?
Then come item enhancements. Being a leatherworker, for me the choice was between using an armor kit or getting a guildmate to enchant my gear with increased stats. Again, I usually went for the agility whenever possible.
But then I hit the high-50s, and things got more complicated. Blue armor was no longer always better than green armor. The stat bonuses started getting better. Many items offer bonuses to more than just one or two stats. And now there are sockets to consider, along with bonuses for actually filling the sockets. Or, bonuses for having multiple items in a set. And in addition to just stat bonuses, there also are pluses to attack power, crit rating, resilience rating, dodge rating, resistances etc.
How does one cope, especially when making the shift to questing in Outland, then Northrend, where much, much better equipment is given as quest rewards? In the early 60s, I often found myself carrying around gear that, as it was, wasn’t quite as good as what I had equipped. But if I was able to get it enchanted, it would be a little bit better. Then I would find an even better item before I had the chance to enchant the second one.
So, I became more stingy with my gear. For BoP gear that’s a quest reward and already obsolete, I’ll just choose whichever item sells for the highest amount (yay, Auctioneer addon). For me, I can’t justify equipping BoE gear if I’m going to find something better in a half-level anyways. Instead, auction it! Or give it to a guildy to disenchant. Do those few extra tenths-of-a-chance to crit really make a difference when I can level quickly without it? Is it even worth keeping spare sets of gear for different uses when you’re leveling up so quickly that it becomes obsolete before you can use it? At least until I hit 80, my guess is no.