I dont know why the 50AE would be a pain to reload or any different than a 45 ACP in a revolver; I suppose its a smaller diameter jacketed design creating the promblem along with a taper crimp.

A snug throat fit caster with a nice deep cannelure ought to fix the crimp issues, especially in a wheelgun. A roll, profile or a LEE Factory crimp die should work, while still allowing headspace off of the case mouth, especially if the bullet is snug in the throat. Taper crimps should too.