Tubeless road wheels won't pump past 80 psi
Road tubeless tires have a pressure limit of 80-85 psi (depending on who you ask). I'll admit I'm surprised that this limit is self-enforcing in this way. 

The fact that you're losing so much pressure in the course of a ride is obviously problematic—the air is getting out somewhere. I don't think you'd be losing that much air through the tire walls. If the tire walls are very porous, you should see a fair amount of sealant weeping through too, and you may need to add sealant until the weeping ends. There are kits for inserting sealant through the valve, if/when you need to do that. Is it possible you're "burping" the tire and losing pressure that way?

Seating the tires often requires a fast inrush of pressure into the tire to pop the beads past the "shoulders" on the floor of the rim; there are special pumps and pressurizable canisters for this exact purpose.