(Spoilers Present)
I can help you with some of your questions.
1) You want to do the ship. If you don't, you miss out on underwater city and a few good magical items. You cannot get to the underwater city from the underdark, but you can get to the underdark from the underwater city.
2) Crashes are frequent in BG2. Out of curiosity, are you using Win98 or 2000?
3)? BG2 manual is vague. Not in 2nd ed. players handbook.
4? You talk to the guy in the temple of helm immediately southeast of you as you enter (name?) It's a quest for the temple of lathander. You may be out of luck because of question 5.
5) The risks of trying to steal. This could also be a bug. I have had a lot of dialogue problems, but they could be alignment related. I didn't have them my first run through with a neutral F/M, but am having them now with my paladin.
6) He's there during the day.
7)? I always have him wield the 2H sword (Lilacor)(it's soooo minsc) despite the 2 weapon proficiency.
In the asylum, there are lots of magical items. With the tokens and the vending machine, you wanted to put 15 tokens in at first. You get boots of speed, which on a powerful fighter are one of the best magical items in the game. boots of speed are much better than the two pairs you get.
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