My suggestion would be to fix the stealth. No Bethesda game really used the stealth aspect well, which can result in quite a bit of lost potential.
1. Unless your character's got low Sneak and Agility, maybe he's clumsy - and can't help but be noticed. Some people are like that. The bull-in-the-china-closet syndrome.
2. True, but what if the NPC is such a dimwit that he never notices anything? Those kinds of people exist.
3. Sure, I agree. Maybe you'd get less disposition from NPC's while talking to them in lower social class gear than they are.
6. I agree. A real guard would make an attempt to keep the peace by intimidating the shady types. Unless he didn't care, or is also shady.
7. Yes and no. Noiseless or not, if you suddenly vanish around the corner and you're not seen soon afterward, anyone with common sense would assume that you're
somewhere nearby. They'd just look harder, practically tripping over you. You can't just pull a Scooby Doo and jump into a pickle barrel.
9. Sure, but too much stealth might knock the game off-track.
I'd like to see myself on posters for notorious crimes.
10. I think it should depend on the sense of the NPC.
11. Nice! So you can roleplay an thief-acrobat. I like it. Toss in some tight rope walking and pole vaulting.
12. I can see this being possible in very crowded areas.
14. Yes and no. You still have to get too close with a dagger. It's easier to strike from across the room than to trip over something right behind your target. Unless of course Sneak is your specialty, then by all means.
15. NPC common sense applicable.
16. Definitely.
17. Not all doors; some are tight fitting, and are of quality design.
18. Some, sure. But if you're a skilled assassin/thief, maybe you can open it more slowly and avoid it.
19. Good idea. Hopefully the chimney is large enough, and not currently in use.
I had a huge post all ready with your quotes included, but it wouldn't let it go through. Said I quoted more than the allowed number.