Power gamers may disagree, but I say play the character you want to play, and don't think so hard about gear. The gear you have should be good enough to level with, and really no one cares about gear when they invite you to join a group (well, that's not really true, but they don't care beyond "twink vs. non-twink"). You'll never see (for instance) anyone /shout "LFM ... except poorly geared monks".
Once you get higher up you can try and find groups that involve killing mobs that drop good gear for you, and slowly equip yourself that way. Or you can find a good partner (eg. a shaman) to duo with, and go for specific pieces that way.
Ultimately I'm a big believer in "level first, worry about gear later", and while being an un-twinked monk might complicate that a bit, I still think it beats playing a class you don't want to play just to farm plat.
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