Been following this kind of problem for two years, have some experience with both 30-30 and 38-55 that shed some light
I think the problem is a tight chamber, too stiff a brass or too thick a neck on the brass.
My 38-55 experience.....
This rifle is actually properly chambered for the 38-55 which has a loaded case neck size of .398 max. The 375 Winchester is .400 I can get 375 Win brass into the chamber (barely), but it won't eject. I can run the loaded case back into the sizer enough to size the neck area down .002, and no trouble. (at least most of the time anyway) If I load 'em hot, once in a while a case sticks. I'm necksizing the brass only, so it starts out a little fat, when fired it don't shrink back as much as full length sized brass, and if the neck is running right at the limit that lets me chamber, but is hard enough to not let it shrink back, and the pressure is just right.....stuck case.
Get some new brass, Winchester, Remington, Starline, whoever, just NOT milsurp. If you're shooting preloads,get new namebrand factory stuff, devoutly avoid cheep stuff like Wolf in your Handi, devoutly avoidammo from small time makers who use once fired milsurp or other range brass to build their ammo on. That stuff is fine in a bolt rifle, wil give you fits in a Handi.