I myself have not dealt with tubeless but have found that some tire/rim combos are crazy tough.
I had Bontrager rims and Continental GP tires. Tough to remove and install. Once I switched to Velocity rims, the tires were much easier to mount etc.
You might try another tire brand on your rims for easier fit.
Same happened with my MTB. Panaracer/Bontrager combo was killer.....Sun Ryno same tires, was a breeze.
I try to avoid Bontrager when I can.