Thanks for the Jig Idea - My jig is a bar with just a single hole spaced so that I can bend the nail over and then bend over the bar end, forming the 'U', then cut to suit.
I crank the vise tight when I peen the ends, but it still slips some.
I install the staples off-set, along the edge of the flat, and stagger alternately, not installed along the bore axis. This (apparently?) should give just a little more metal to minimize the danger of drilling into the bore.