An interesting dynamic here: I am on a save patched to 1.9. I was playing on a patchless save for a long time.

I pickpocketed from every NPC in Riverwood (except children) on both characters. With the patchless character, I had 3 separate hired thugs encounters, with contracts on them from 3 different NPC's from Riverwood. All before even leaving Riverwood.

On my patched character, I have never gotten a hit put on me.

Any connection to the patches, or some technique to getting more contracts put on me?

I actually like the hired thug encounters. I collect the contracts to see how many I can get.

I get them a few times a week. I am using patch 1.9

Interesting.. I am on 1.9 with a character, 108 hours in, and have only gotten 1.

Quite a bit of pickpocketing, too. I don't get it.

Try killing Nazeem. his wife will send a contract.

Well, I particularly enjoy the randomness of the contracts, and the fun of not knowing who hired the thugs until I read the contract.

Not getting too much of that fun this character..

I killed someone for the DB , some stables worker and got attacked once by thugs hired for her dad/husband. when I walked away I suddenly noticed one of those hired thugs was following me , now everywhere I go he follows me and fights for me , like a follower.. I have no idea how this happend but he doesn't count as a follower I walk around with aela and a hired thug who fight for me.. I hardly have to do anything at all

I've only gotten it one time on each character I've ever played as well. Playing on the Xbox 360.