Welcome to the forums, Manny!
Anyway, regarding all the loot and whatnot, here's how our last run broke down:
We had only three people really able to dungeon-dive: Galeesa, GPH, and me (El Juan). El Juan (my multi) essentially beat every boss except for Chester, because Hamster decided to get a good whack at it. Back then, I (he) was only a level 23 sauceror or so. Now I'm almost Lvl 31 on that, so things were tougher. The loot we got (as little as there was, because I couldn't handle a whole lot) was divided mostly between Galeesa and GPH. I took the sauceror stuff because that is my exclusive character and I will not ascend with El Juan again. So, Ol' Scratch's stuff mostly went to me, and I divided everything else on lines drawn from ascension history. The Hoboverlord gear was divided between Gal and GPH also, with El Jaun getting nothing on that one.
Essentially, El Juan is running the dungeons for fun and profit, as best he (I) can, and dividing most of the loot for everyone else. The sauceror stuff I have a particular want for, since that is my class. The Hoboverlord stuff is REALLY nice, but I wasn't going to be selfish enough to claim hobo stuff for a multi. I just took the crap no one else wanted.
Now that we have four people (three really) runninng the dungeon, things will get a bit more complicated, but I'm sure we can work something out like GPH said. I do agree with your point about "hoarding" items though. But that won't be a problem for a while. We're noobs at this.
Someday, we hope to have enough cash to run these dungeons more often, but they are expensive to start, that is for sure.