I would specialize in crafting but I will just be a bodyguard of the caravan, I wouldn't mind questing or scavenging items for the caravan, I thing we should also sell items to NPC's as-well.
I think we should all get a small cut. I wouldn't mind 10% even though I have the most dangerous job of the guild.
One of us needs to specialize in speech
Both of those seem like solid ideas. Because I'm guildmaster, (or so it seems in this situation) I can divide the earnings amongst us. I don't know if there will be a speech tree, however, I am more than happy to spec into it.
The original purpose of the guild in my mind is that we support each other in order to make the most valuable items possible. For example, you make a Daedric sword (If you specialize in Weaponsmith) and you give me the sword for the time being. I specialize in Enchanting, thus I give the sword a high enchantment. I then sell the sword for a high price to an Aldmeri Dominion member, us splitting the profits evenly. Therefore we both make a lot of $ as well a support the war effort from behind the lines.
However, those who both venture out to get rare crafting materials, and rare loot, will be rewarded fairly as well, getting paid by the guild itself for their efforts, creating a very lucrative trading guild.
Bodyguards, a new idea in my mind now, will guard a crafter as the person searches for items, or guard the group as they travel from town to town, selling the loot. The bodyguards will get a good reward as well, to encourage the protection of the weaker members, or more fragile mages, (I plan on being a mage myself.)
Overall, the way I picture the guild in my mind is a collection of like-minded Khajiit all in search of fellowship and the shiniest material of all, gold...