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Maybe I am off on this and how I understood....
your post but I always deprime and flare the case opening and then use a case gauge to see if the case needs trimming.
If it does I insert the case trimmer which has the needle like arm on the end that properly measures the case length. Now on my 357 cases or even my .38 cases you have to feel around easily to get the stem/needle sized end to fit in the primer hole then it slides all the way end. Then I turn the trimmer to size the casing.
Now sometimes the case mouth is still slightly tight and you have to use slight pressure to get it inserted.
Hope this helps........a video would be better of course but words or direction may help.
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