Hey Molster,
I don't have any advice on how to solve the mechanical issues you are having with the pick (I will leave that to Mr. Schlegel!), but I will remind you of one thing that I see Mike O. mention fairly often. Keep it fun.
If you are stuck on something like this to the point that you are not having fun, work on something else. This will be there and you can come back regularly. Make the pick a small part of your practice routine instead of the main focus. Go back to basics for that part of your practice and don't try to do the same things with the pick that you can do without it.
I know a lot of this is mechanical and physical, but I really suspect a lot of it is mental -- at least the frustration part of it. You're taking it very seriously, and after all, it's just the guitar, y'know? :-)
Anyway, good luck and don't be too hard on yourself!
Dave...
It takes as long as it takes unless you quit - then it takes forever and you will never get there.