1. IMHO no, he's very weak. Greater werewolf is good, but not worth it.
2. Get the Improved Jaheira Romance patch and be prepared to use CLUAConsole since its very buggy. The romance runs on real time not game time so just leave the game running for a while to get the next dialogues.
3. Don't know, you can only be a wild mage in TOB (I think?).
4. Viconia will dump you but it gets better in TOB. Don't know which is better, but Aerie's is very easy and not buggy; good for beginners.
5. Aerie is good as a mage/cleric, Jan as a mage/theif. But they're multi. Imoen is good, she has enough thieving and is a dual mage so can cast more spells than Jan.
6. Only the protagonist can have a stronghold, so just one per party.
7. Keldorn is the only one who can use the best 2-handed sword in the game, they get the same amount of proficiency.
8. Depends what weapons you've got, how many real fighters you've got, and who you're fighting. A thief/mage should definitely have a ranged weapon and stay out of most melee. Depends how you play.
9. Don't know.
10. Whenever you need a boost and you don't need him to cast spells etc.
Hope I've been helpful