So I'm stuck at the point where I need to hire Orris and look for suspicious activity. I've already did this once, I saw him do something suspicious but I didn't have enough skill points to get the information when I spoke to him. Now, in subsequent tries when I follow him we make it through the entrance to freeside, but then he just stops at the intersection past the liquor store. I have a save point right before I hire him, and I've tried quitting the game and reloading but he doesn't seem to every do anything. If I wander too far off he leaves because I strayed off course, and if I try to talk to him he says don't distract him.The one time I did get it working, he killed 2 enemies who came up to him, but nothing suspicious happened. It said that this section of the quest was completed but I couldnt do anything else. Anyone experience something similar?

go back to were u hire him and walk with him to the point when shoots four thugs when he has shot then talk to him and ask him about firing three shots but killing three people. then go to the bodies and if u have your medicine skill up to tweenty five ( i think it's 25 ) and you'll notice there still alive that should be enough to tell the king.

Thanks, unfortunately though I've just tried it again several times and each time and he never shoots anybody. He always stops at a certain point, I can run ahead to the strip entrance and then he will eventually come up to me and tell me we have arrived. Maybe this will be fixed in the patch, unless there is something else im not seeing. I saw that the bodies from the very first time I did it are still there, maybe I need to wait for some time in game to pass.

The same just happened in my current game. I former games he started "shooting", but now he does exactly that, what the OP described:
He stands in front of the "thugs" and aims with his pistol. When I try talking to hi, he answers with this "don't distract me"-thing.

Any idea why such a simple, but important quest can be broken?

As someone else mentioned go back to the point where you hire him i think you have to have so much inteligence to say you fired 3 shots their are 4 guys here, or if you have a medical book examine the bodys of the guys he shot and it will tell you they are faking being dead.