I haven't seen a clew screw rip through a fin pocket before, but have had those brass nuts unwind down the screw. I believe Hobie now nicks the tip of the screw to stop the nut if it accidentally gets to the end. Nevertheless, I always use Locktite on the brass nut now if there is any looseness of movement just to maintain the proper clew adjustment.
It's possible that the ripped pocket started as the nut was unthreading while there was little left to contain the screw. Or perhaps it was a manufacturing defect like a hidden air pocket. Have you shown this to your dealer? I believe Hobie parts are warranteed for 1 year, so that may be your best solution. If not, you can nick the end of your screw with a set of dikes and double check the Loctite from time to time.
BTW, you might try loosening that fin so that it is just sitting the "pocket" about 1/8". It will make pedaling much easier and probably speed you up as well.
