If you wanna go troll, go troll; each race has its merits. If you're going to be grouping all the time, try and avoid outdoor zones like Ro and Oasis, as dungeons have EXP bonuses and better loot. I would head into Upper Guk as soon as you can. Some loot to keep an eye out for is the savant's cap and bloodstained tunic/mantle in Unrest, split paw hide gloves from Infected Paw, embroidered black cape from Lower Guk, and runed mithril bracer from Solusek B. However, you will easily be able to buy these items and better ones by just earning money through loot and going to EC. I've built up something like 5000pp by level 41 by just selling loot to merchants and finding the occasional expensive piece of loot I'd sell to players. The combined worth of the items I mentioned is a few hundred plat.
Gear-wise, my suggestion to you is to get a full suit of large banded early on, some silver and electrum WIS rings/earrings, an OK weapon (I went with Cold Iron Morning Star first and then Gloomwater Harpoon), and an OK shield (Bark Shield has been good to me). That'll do you fine until level 30, at which point you can go quest all your totemic (though you'll need help in a couple places, e.g. Kedge). By that time you'll also start to accumulate decent sums of money and can buy stuff at EC.
Really the only reason I've been finding gear upgrades while EXPing in dungeons is that I've been hoarding my money for other, more gear-dependent characters, rather than spending it on my shaman.
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