Recently I've gotten back into Heroscape as my school responsibilities have cooled off a bit. My son and I have been playing a game a day 5 days out of the week. He is big on the Hobbit and LOTRs and currently reading through the Hobbit. So I picked up Heroclix figures Gandalf, Gimli, Strider, and Legolas.
Of course getting LOTRs figures brought me here to find out how to bring them to the game.
Reading though what you have done so far I have to say you have accomplished quite a bit and I am impressed what you have done to the development of an expansive new master set. I particularly like your consensus on Gandalf.
Since this first Master Set will be centered around Fellowship of the Ring, I suggest special
Divisions of Heroes and Squads perhaps unique to this portion of the story. As the game progresses to further along the plot line alliances change and paths diverge. These considerations may help in placing order markers and movement.
All that being said, I suggest that you group the four Hobbits into a unique squad and then later divide them into 2 figure unique squads. This will greatly help in movement and attacks since thematically these characters typically act together. This suggestion isn't original to me in that previous discussion has considered similar treatment of the 13 dwarves of the Hobbit storyline.
Anyway, Great Work! Hopefully with summer your project development will be underway with full steam ahead.