my initial guess is that looks like its getting dragged upward. you see the burr on the 12oclock and the fact the 2 o'clock one is bent under itself. Then dish, if any on your top cap may be starting to make contact with it
something i have found is that every now and then i try to fit a star nut and they are slightly under sized, meaning that when you adjust the headset it seems fine but over time can move, causing the headset to come loose, as has been pointed out above, a part of the star nut has bent over on itself which suggests it's not a tight fit, might be worth replacing it just for the sake of it
Crank bros does a really low stack HS. I used one a bit back after running into the short steerer prob.
Sorry, cant remember an actual model, you'll just have to search for yourself.