Yeah, you can put your skill points wherever you like (level permitting); class doesn't mean much for most things.
I never had a problem with the outdoors. Or indoors, either. The auto-map is pretty decent, and the teleporter map is also a great help. You shouldn't get lost anywhere.
Yep, always accept quests. You have to take George's, else you won't be able to buy/sell with him. After you rescue the guy who's half-frozen, you can ask his permission to take herbs from the garden. Also (hot tip) while he's still "on ice", you can slip into his house and take what you want
Nightowl2