A 2-class group: who would you pick?

[Treesh]

Couple things.
Odd that you would pick probably the ONE combination where same-armor classes CAN work together. Had you said Rogue / Hunter, I would have agreed, or even more Hunter / Druid, but Rogue / Druid would seem the perfect matchup. Leatherworking supplies two things: Agi/Str/Sta, or Int/Spi/Sta. Druids, generally, and especially in this combo, will favor the Int/Spi/Sta items over Agi/Str because they'll be more focused on casting. Their inherent shapeshifting abilities allow them to Tank / DPS if need be without massive reliance on damage-boosting stats. The Rogue, having NO mana at all and rarely if ever wanting to swap Spirit for more Agi or Sta, will focus solely on items that add to their damage and life. Agi, Sta, and Str are their number one priority, which only a heavily-SHapeshifting specced Druid would ever want (which is rare, and goes against the role the Druid is meant to fill in this pairing).

So, IMHO, Rogue / Druid would be not only an incredible combo (as has been said), but one WITHOUT worries of splitting the loot. What's more, a Rogue with Leatherworking (such as myself) can make plenty of Druid-oriented Leather, while a Druid with Alchemy can make some potions that will help out both characters, and especially help relieve the Druid's need to heal the Rogue (due to potions) and allow him to focus on damaging spells, if need be.
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There are very few times when both Taranna and Eth were drooling over the exact same piece of equipment. The only time there was a conflict was when GG was looking at something for his feral gear set and even then, it was easily resolved since usually there was spirit or more strength than agility so it goes to the person who uses strength more - the druid.

I disagree completely with shapeshifting going "against the role the druid is meant to fill in this pairing". The druid's "role" is to be fluid and do whatever the situation calls for, not just being a heal bot. That means the druid shifts from cat, to caster, to bear whenever and wherever needed. The feral gear is just as important as the caster gear when paired with a rogue. GG only rarely stays in caster form because things go quicker and safer if he goes cat for DPS on weak critters or bear for tank for those hard hitters and if we need crowd control outside, caster form. The bear can tank much better than the rogue can and the rogue can help ease health concerns by liberal use of stuns. If your druid isn't changing and adapting to the situations around you, you'll get killed more often than not. Use the wide range of options available to the druid and it will be an absolute blast for both the rogue and the druid.

Edit: I also forgot to mention that when playing in cat form with a rogue, there is next to zero downtime on non-hardhitting critters. If one starts to get hurt in the fight, the other one opens the next fight. There's no need to heal, no downtime.