Hi Midnight -

I'm wondering if a different pick might be worth a try.

Some of what you are talking about has to do with the nuances of your hand's angle as it plucks the strings.

But if you've tried to eliminate the problem without success, you might also try experimenting with different styles of picks - something that allows you to hold the pick in such a way that your nail stays out of the way.

Me, I prefer a particular kind of pick that has more of a pointy end, over the standard teardrop shaped pick.

Maybe a little trip to the music store and a couple of dollars worth of picks?

Keep us posted -

Happy New Year!
-Lisa