You can trim any brass with any case trimmer, but why do you feel it will solve your apparently tight fit in the chamber? (You said the cartridge won't "drop in"), rather than fail to chamber, which implies they don't fully seat. What type bullet are you seating in the case, does it have a crimping cannelure? If not and you attempt to crimp (either a roll or taper), instead of crushing into the bullet or its jacket, it may be making a slight bulge in the case along the crimp edge, making it too tight a fit in the chamber. You'd either need to switch to a plated bullet that has a softer jacket, or straight lead bullets, or jacketed bullets with a cannelure, which is designed to be within the seating lengths for the completed cartridge. You may also be putting too much crimp into the bullet.
One other consideration about trimming brass is how much you're taking off. Take too much off (below the minimum SAAMI length) and you're effectively decreasing the case capacity, which will affect ignition pressures, which dictate a decrease in the powder load for a specific performance, or to be a safe load. There's only 0.135" difference between a .38 Spl. case and a .357 Magnum case length, and putting a magnum powder load into a Spl.-length case could create overpressure problems.
Of course, the brass needs to be within SAAMI specs for length when you process it for loading, which may mean trimming the cases back to spec before loading them. I can use my handgun brass many times before it gets out of spec for length. I start worrying about splitting the case mouth from too many sizings before I have issues with length, and that even extends to semiauto cases that headspace on the case mouth.