Here's what I'm considering so far:
- Dwarf Fighter/Thief multi-classed character (True Neutral?)
- Human Fighter. After reaching Level 8 or 9, dual-classed to Cleric. (Lawful Good? Chaotic Good? Chaotic Neutral?)
- Human Cleric (or maybe Fighter). After reaching level cap in Pool of Radiance, dual-classed to Paladin in Curse of the Azure Bonds. Lawful Good.
- Human Cleric. After reaching Level 9, dual-classed to Magic-User. (Lawful Good? Chaotic Good?)
- Human Magic-User. After reaching Level 9, dual-classed to Ranger in Curse of the Azure Bonds. (Chaotic Good?)
- Human Magic-User. Not dual-classed. (Chaotic Good?)
If it helps, the Gold Box games use AD&D 1E rules, more or less.
By the way, I'm probably just going to avoid Hillsfar altogether.
EDIT: Here's something I wrote over on Google+:
"Unfortunately, there were a few self-restrictions I did want to abide by if possible (and if it's not TOO foolish to do so), which I forgot to mention in my blog post because I had a brain fart. I was hoping to have one person in the group be a race other than human, although I don't really need more than that. I also wanted all of the classes (the six in these games, that is) represented in the party in one way or another, and I was hoping that no two characters would be EXACTLY the same, class-wise, although it's fine if they're close. Other than that, I think I'd be up for about anything, but those are arguably already some major restrictions on my choices. I'm fine with giving the characters all 18s in their abilities, at least, since from what I hear about the hardest fights in the later games it's either that or reload a lot. :P"
EDIT #2: After some helpful feedback from ckdecember gaming on Google+, I've decided that it might be a good idea to wait until Level 16 or 17 before switching my dual-classed characters to their second classes.
EDIT #3: Here's what I think I've settled on:
- NG Dwarf Fighter/Thief (multi-class) - Selena
- CG Human Fighter 13 ---> Magic-User - Flame Princess
- NG Human Fighter 13 ---> Ranger - Rhona
- LG Human Cleric 17 --->Paladin - Alice
- CG Human Magic-User 18 ---> Cleric - Kendra
- CG Human Magic-User (not dual-class) - Melissa (I'd name her Étaín, but I doubt you can do fancy accent marks in the game)