Wait a minute there PJ, ......
You Lube, Size, and De-Prime ....... BEFORE?? ...... running it through your Dillon??? I mean it's really none of my business, but ................ Isn't that what the first position on a Dillion is for?? Well, to resize and De-Prime. Squirt the lube on prior of course. Well, anyway, 44-40 or 38-40 or 32-20 can be a challenge to load. After a little trial and error ..... easy peasy.
I do fully agree with, recommend, confirm, suggest, and put fourth "crimp as a separate step." It may be found the RCBS Cowboy "seat it, crimp it, spit it out, die will crush a bunch of 44-40 cases. Personally, I like "Redding Profile Crimp" dies. Doesn't mean they are the Be All, End All, worlds best, etcetera, etcetera, etcetera (famous movie line), just that I like em. Lee "Factory Crimp" is pretty good too (I have heard) although I have never own'd one.
Take your time. Don't use CCI primers for anything and if your not sure ....... ask.
Coffinmaker