I feel like, at the very least, the option to steal more expensive weapons should be available to the dedicated pickpocket (as well as more money).
Lazymonk does make a good point in that stealing a bozar from the guard in F2 did seem a bit unfair. For me it resulted in save scumming to get a really good item, then selling it for enough money to buy my favorite weapon, the .223 pistol. But I strongly believe that that type of gameplay can be very fun if done in a fairer way - so for a person who invests a lot of points into pickpocket and stealth, they should have the option to steal heavier weaponry, and would be able to succeed in stealing it.
The same should go for money - as you become a better pickpocket, you are capable of stealing progressively more and more money from merchants that an ordinary thief couldn't get away with.
Currently I dislike the dynamic of filling up a bar and not being able to steal anymore, simply because it seems quite unrealistic. But I understand that something like it is necessary to prevent stealing from being either overpowered, or leading to save scumming.
I feel like a more reasonable approach, might be to allow the player to only steal a certain amount from the merchant (or other NPC). After that experience, the NPC will become more guarded, and his remaining items will be harder to steal. So only after you invest more points, will you have the option to steal those items available again, in addition to any larger items in his/her inventory. Since most characters will only have 4-5 items on them (where an item could also be a stack of money/ammo/etc.), I feel like this inventory categorization wouldn't take too much time.
Either way I hope Styg finds a way to incorporate an interesting but fair pickpocketing system into the game, which is hopefully a bit more realistic and allows for more progression as a pickpocket, so you could go back to older areas and still use the skill.
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I like the suggestions for improvement on money in general, certainly with the locked chests at least. Also I am all favor of more skill-related quests.
Money is definitely hard to come by. I'm not even sure what its like to play a character that doesn't invest as many points into barter with each new level; I shudder to think at how difficult it would be to even buy one or two repair kits. Thankfully now degradation rates are reduced so its probably not as hellish as I imagine