As near as I can tell from the OP's interior hull photos, the Win hulls in question are tapered. Basically, the same as AA HS hull interiors. If so, gonna be hard to find a modern era wad that lacks the large compression zone with shot cup large enough to allow that much payload. More on this below.
So you may be back to that Win AA Red wad......pile in the buckshot, then start looking at overshot cards to fill the space, or since shot is going to be running proud of the wad anyway, drop a 20 gauge nitro card in bottom of the shot cup below the buckshot. That will take up about 1/8" of space. Option B is to switch over to an overshot card and roll crimp. You can pretty much crimp anything that way.
You can do all these space test trial runs using a fired hull. Leave dead primer in place, drop in powder (won't go bang), wad (seat it lightly), then start dropping your shot and spacer combinations until shot column tops out where you need it to for a good crimp. I've even been know to replace a known volume of powder with equal volume of fake power, like walnut shell media used to tumble clean rifle brass. Hull is graveyard dead that way. Only thing you lose when cutting results down to recover components is the spent hull.
Then there is option C. Switch over to the true straight wall hulls like the Fiocchi, then use large payload capacity wads intended for non-toxic shots. Wads like the Mg42 and some of the other exotics. They have a small crush zone (or none at all) and allow a huge shot payload. The interior of the Mg42 is tapered at the bottom of the shot cup, so won't work (won't stack right) for large buckshot like 00, but may for smaller #4 buckshot. I have a couple of these options, and if time permits later today, may try 27 pellets of #4 buck in what have and see where that goes.
Whatever you wind up using, once you wonder out of bounds and start using 1 1/4 oz payloads over enough Longshot to get it moving, using such exotic combinations of components is a ticket to disaster. I wouldn't go too far down that road without getting it tested. Kinda like the difference between lady fingers, firecrackers and cherry bombs. When things go wrong, the difference is pretty dramatic.