Getting the rotations down for multiclass teams isn't as much of a bear as some people make it out to be. There are certain specs that rely far more heavily on proc-based abilities which makes them harder to work into a team -- we have covered those in other threads about cataclysm.
In WoW, you have 4 armor types: plate, chain, leather, cloth. I understand your rationale wanting to cover all the drops but there is another twist: for each armor type, there are at least two "stat groupings." Example: For plate, you have one that is caster-based (int/spi/stam/etc.), one that is tank-based (stam/dodge/parry/block/str) and one that is DPS-based (stam/str/hit/crit). This makes the odds of you getting the wrong spec about as likely as you getting the wrong type of armor. And once you get into the higher instances, you're going to gear up faster buying crafted/BoE gear and then Justice point gear than you will just through drops, IMO.
Short answer: play what sounds interesting, as the drops don't matter as much.
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