So, I'd like to play a bit like a thief. But...I don't like stealing from generally nice people. I'm wondering where I might loot from some less...likeable NPCs.
Any good places to hit that I won't feel too bad about?

Windhelm and Markarth both have some particularly odious people that could use a good thiefing.

Nazeem in Whiterun....

[You know.... the one of whom his wife Ahlam says, "Looking for my husband Nazeem? Check the Jarl's backside, that's where he stuffs himself these days." Which caused me to lose a mouthful of good burgundy all over my keyboard - thankfully covered by a KeySkin.... and then have to spend ages trying to explain why I was convulsed in hysterical laughter to my non-gamer husband.... *sigh*]

The older couple with hired body guard in tow making their way to windhelm ( I think) for some rich wedding to increase their social standing bragging about all their expensive wedding gifts. They don't deserve it, they just flat out beg for it.

The Black-Briar family in Riften is disgusting and deserves to have all their wealth taken from them. And the Silver-Blood family in Markarth is the same way. Good for nothing, greedy, ruthless is what they are... particularly Maven Black-Briar and Thomar and/or Thongvar Silver-Blood.

I still cannot figure out what messages are in these words...

I hate Maven more than Grelod, I really hope Bethesda can provide a questline which allow us to wipe out Maven influence.

I pickpocket Maven until she is practically naked

I also wish to see a list of "bad guys" so I know which NPC deserve to be pickpocket.

I so miss Gray Fox

The older woman who isn't well liked in Windhelm (she's a nosey nancy and we all know what happens to the curious types). Adelaisa Vendicci I think is her name... she has a residence somewhere in the city.

Definitely steal from Belethor that sleezeball. He said he'd sell his sister if he had one (in that case he should move to Morrowind cerca 300 years ago so he can get all the benefits of slavery and not have to deal with the Nerevarine messing up his business or that whole Red Mountain explosion thing that happened six years later...). Although he doesn't have much worth stealing sadly.

I'd also make it a point to steal from the White Phial. That old man is a scrooge, a miser, and a cheat.

The guy with the Mythic Dawn museum in Dawnstar, pretty sure no one likes the murderers of Emperor Septim.

The tailor in Solitude run by the two elves, Radiant Raiment. If you start to leave you can hear them arguing about customers and both seem to share a disdain for the local population.

The Blackbriars, the Silverbloods. That drunk Nord in Windhelm who goes and yells racist things at the Dunmer all night long. That Nord who runs the docks in Windhelm who pays Argonians ridiculously low wages unless you convince him otherwise. The Battle-Borns in Whiterun, saving a few of the younger members. It sounds like you aren't doing Thieves guild, so the guy who runs the Meadery outside of Whiterun is a real jerk. The lady who runs the clothing store in Solitude. All of the Thalmor at the Embassy. The Thalmor contingent in Markarth are there to hunt down Talos worshippers, and are real jerks besides. Really any Thalmor patrols you come across.

Sneak into bandit hideouts and steal all their things, then reverse-pickpocket them to the beggars and the Khajiit merchants. If you've got those Alik'r soldiers harassing random Redguard women on the roads, then them too. Those two guards outside of Riften that try to shake you down when you first enter. The Thalmor guy at the mage college. I remember the Dawnstar Jarl being a jerk too, and the one in Falkreath (though he probably doesn't have much to take). Any guard that sneers at you about sweetrolls.

Vittoria Vichi or however her name goes in solitude, take that quest involving her from the stall keeper if you fail the persuasion you'll see why she deserves it.

Ah yes, I also did that. Pickpocket bandit does not need to worry about bounty, and even you fail you can calm them and pickpocket again

The beggers of Skyrim.

The guy in the meadery in the plains of Whiterun who told me to p!$$ off if i didn't want to buy any alcohol.

Actually his boss is more deserving. I LOL'ed out loud when the employee told me to POQ. lol

These, I dont care about quests,but making them unkillable pisses me off. Seriously I havent killed ANY blackbrirs, they just dont [censored] die.

Reverse pickpocket a frenzy poison onto the beggern in Markarth, he wants you to rb a temple of Dibella.

It involves a certain advlt material, if you know about 'em.
Haven't realized it up until now either

Thonar Silver Blood in Markarth and Maven Black Briar from Riften, they're asking for it.

And can you steal from Ulfric too? I like Stormcloaks, but don't like Ulfric. Can I just assassinate him and take his position?

Arent't they all? Thieves keep thieving

pickpocket all the weapons and armour from the people trying to escape the jail and then reverse pickpocket decent equip and pots onto the guards and see if the escape stil works ( i have yet to try this myself as i am not sure if the escapes are temp esseisial during the escape or not.

i really wana try this once and see if the guards can actualy prevent the escape by kiling them all while i hide in the corner watching them die!

I hate that miserable wretch. My assassin followed him after he told me I never make it to the cloud district for the millionth time and plunged a dagger in his back.