Well i am not only doing well on my thief character i made, but also having fun. So far i have 100 sneal, 40ish onehand, 70+ pickpocketing, and 25 alchemy. I put enough points into pickpocketing that i can put poison inside peoples pockets. I have a few questions regarding this type of skill:
1) Can i place poison inside enemies pockets? (I.E. Bandits, wolves, giants, etc?)
2) Would it be an effective method to killing enemies i cant kill with my weapons? I have a hard time considering im lv20+ with a glass dagger. I say this because my character is more of a sneaking guy, he uses sneak and silemt killing methods, but i'm not sure if this use of poisons would actually be effective enough to kill people and not be heard/seen doing it.
Thanks for any replies.

You can poison only those enemies you can pickpocket items off from, so not animals, creatures or Draugr. But as undead Draugr have poison immunity anyway. So do vampires.

Poisons with highalchemy do a lot of damage, but high level enemies do have a lot of HP too, so one poison is propably not enough. On the other hand, they don't notice you poisoning them. And you can give them a paralysis poison and kill them when they're helpless Then again, sneak attack with a weapon poisoned with paralysis does the same thing

so should i even put points into it :/? It seems useless unless fighting humans. What a a bummer.

You know when you find something good on an animal, well animals don't have pockets so you know..... if you were to place them on the animal you would have to get fairly close to it.
Not that you can, but if you could that would be how it is done.

Yeah, haven't found much use for it myself. Though placing a frenzy poison in a bandit's pocket is good for some laughs

Ehh, i've already put points into pickpocketing for he 100 capacity increase and poison sabutage. I think i'll just keep it. If i don't like it ill restart my character. I can pickpocket briar hearts and 1hit kill them ^__^ !

I played a thief/assassin all through the game... and I've never used a single poison. Not once. In fact, Alchemy was one of the LAST skill trees I maxed to 100 - and that was for fun/perk points than necessity.

Once you get the 15x damage buff from the 1-handed tree for daggers, you can pretty much one-shot anything in the game if you sneak up to it. And if you're close enough to pickpocket them - then you're close enough to just knife them in the neck.

Yeah, my assassin is a master in the art of pickpocketing and poisoning. Using this method is a great way to spice up play and it's a very quiet way to take down an enemy. I personally enjoy taking an enemies armor and placing a frenzy potion inside their inventory. They start fighting one of their comrades and fall to the floor cold a few seconds later. It would be nice if after they take down their buddy they start freaking out and shake with nervousness, instead of going about like nothing happened. Hopefully they include something like that in later games though.

You can place poison into any pocket that is of a playable race.
Bretons, Nords, Dunmer and the rest, but not monsters, undead, constructs, daedra and others.

You can have a lot of fun placing poisons on people.
Paralyze is always a laugh, slow is very useful and my absolute favorite pickpocket move has got to be picking the heart right out of a Briarheart's chest and outright killing him.

Whoever came up with that deserves a gaming medal.

A small tip:

This.

I hate when I sneak attack someone with an arrow, and they give up looking for me after 30 seconds.

"Huh, well...I guess it was just my imagination that I got hit in the side of the neck with an arrow. Doubt someone would actually try that in real life. I'll just go back and stand by my designated spot."

I hope in future games that either A. They don't stop looking for you until they're dead or B. They'll run and hide.

Yeah, those effects are pretty great. I just wish they had some sedative to make enemies fall asleep.

Fear and frenzy potions are also good for the pickpocket/ sneak character.
Sleep would be nice though. I love being a vampire necromage and its nice to see a sleeping dinner.. I mean bandit.

You can oneshot anything you're difficulty is low. Being on master difficulty is a little more than oneshots. Either that or my iron daggers are the problem >_