When roll crimping, you'll want to have consistent case lengths, otherwise the crimping will vary. Generally, I don't measure/trim most pistol brass, but for consistent roll crimps, it might be worth the effort.
Many die manufacturers will provide shims to allow for die adjustments with different calibers (.38 Spl/.357 Mag., .44 Spl/.44 Mag., .40 S&W/10mm Auto, etc.). You would use the thin shim when adjusting your seater/crimp die for.38 Special. You adjust the die without shims to where the proper roll crimp is applied. Add the thin shim to allow the roll crimp to avoid contact when seating the bullet in .38 Special. Back off the seater top punch and remove the shim; now roll crimp your rounds.
When loading .357 Magnum add both shims while seating your bullets. Remove the thin shim to apply the roll crimp.
The shims allow for a one-time die adjustment and done.
Generally, you don't want to be applying the crimp while seating the bullet, hence, a two-step procedure.