Keep the shackle pin end forward, and the drogue thimble can rotate around the rounded end of the shackle.
Triple (or so) the thickness of the tab aft of the transom with seal welds so the tab is as thick as the eye of the shackle.This will strengthen the tab and give a wider bearing surface for the shackle pin. The shackle pin will be maintained in fairly rigid alignment with the tab. (note if I take this route I might be inclined to go to a 3/4" Crosby shackle and really make it overkill, as this is the weak link in the whole arrangement)
Torque the heck out of the bolts holding the tab to the hull and the G10 bonded inside. (note this is a well made hull, so I suspect this is overkill but what the heck.)
The bridle will join the drogue at a point about 20 ft aft of the transom, which is about the 2.5x transom width recommended by Jordan, and by happy coincidence it is also about the point where the natural sight line of the sides of the hull converge. In other words the load will be aligned with the tabs, at least when the bridle is evenly balanced.
As Jon says this may all be moot but I think I will feel a lot more secure having this tool. Unlike the Westsail 32 I sailed in the Southern Ocean, the Nordic seems to have a lot more potential to surf down seas at speeds higher than would be safe.
Thank you both and welcome any other feedback.
Max