Boar, you're a genius! I forgot all about pneumatic spearguns needing to be filled with air!

You can get a speargun pump for about $30.
That isnt what inspired me the greatest, though. Your mentioning pump cups reminded me of my Crosman 1377. The pump tube on that has a .625" ID, the same as the OD of 1/2" copper pipe. That means if I use a copper repair coupling as the pump tube, I can epoxy a 1377 pump cup on a piece type L copper pipe with a T fitting on the other end and a couple of short lengths of pipe for a grip and I've got a pump. At the very end, I'll use another T fitting, with 1/4" NPT fittings on either side, one for a gauge, the other for a check valve and QD. To reduce headspace, the copper pipe that joins the pump tube to the bottom T fitting will be filled with epoxy and a small hole will be drilled to permit the air to pass through! The biggest repair coupling I've found is 12" long, so the pump will be short enough to take in the woods. It will have 2.5x the diameter of the shock pump I normally use and 2" more stroke, giving it almost 8x the volume! This will cut pumping down quite a bit.

400 psi only requires ~123 pounds on the handle, so scrawny little me will do just fine pumping on the high end. Thanks, man you gave the breakthrough I needed! I'll post pics when I get it done.
BTW, those pump cups are available from Crosman by calling them at 1-800-724-7486 and asking for part #760-140. Order about 10 of them and you should have all you'll ever really need.