Bah i'll give it a shot...
Gandalf:
Beren87 cause hes always lending a hand...
Aragorn: Son of Numenor, to me is a strong-willed character, so he'll fit in with aragorn
Boromir: well i guess
Morsul could be boromir, each have inner evil
Legolas: Who better then the agile
Legolas of the downs!
Gimli: i think
Telchar can fit in here, having different moods during the days...
Pippin: i will go with
Perky here...
Merry:
Tom Bombadil can go here cause hes always cheery until he gets wacked in the head to pay attention
Samwise: Faithful, like
Pio...
Frodo: and the winner is.... Esty!...see top for reason
There ya have it folks, i didn't put myself in cause i don't really know...thats for you to decide!