I dunno about all that bog, it sounds a bit untidy and heavy...
Here's a similar shroud attachment on my IC. There are many more than two layers of unis over the loop: I think I have about 6 pieces of the normal narrow unis, each folded in half to go through the loop, and then fanned out over about a 90 degree angle over the topside You can arrange the fold so that it unfolds andby the end of the unis its single thickness. Whilst you have a special issue with compression on the turn of the gunwhale, provided the base structure is filled back up and has a couple of layers of cloth over it to bring th strength back to what was new then I doubt you'll have an issue when all the fannned out unis are distributing load. I rebuilt the PlusPlus shroud anchors in much the same way and didn't do anything to the core, and that had just as shallow flares as your boat...
Consolidating the laminate with ply covered in parcel tape and peel ply underneath of course.
A layer of cloth on the outside over all the unis.
That's the front bulkhead now glued in against the shroud anchor...
With the vertical topside of the Canoe the unis go each side of the skin. With the PlusPlus (and of course the Dog) most need to go on the outside. I put a couple of the layers of unis over onto the inside of the skin on the PlusPlus in order to give some strength for odd eventualities, turning the boat over singlehanded by means of string to the garage roof, tying the boat down via the shrouds, other odd stuff... You don't want it to be able to just peel off if it gets a load from the wrong direction.