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Does my Leica need a CLA or is it user error?

Then your 1933 III is not stock, while the OP attached photo reveal non modded Barnack body.

Leitz only fitted a fix part way through IIIf production, the fix could be retrofitted and is easily seen as a finger point up part way along the base plate.
Maybe the pressure plate springs are slack or a shard of film is wedged but more likely film misload?
 
I generally use the take the lens off to load method, and still am getting these results. I sometimes prefer to use factory cassettes, so FILCA is somewhat out of the question. I'm not above rubber cementing in a nylon spacer or something though.

I guess the next logical step is to try cutting the film "properly".

I could get a knockoff soviet camera or a more modern M series, but I simply enjoy shooting with the older ones more.