I have noticed that certain brands of .38 Special brass have tight primer pockets, most notably (but not exclusively) S&B. I generally ream them. I have a primer pocket swage set also, but I prefer reaming them. I also use a larger drill bit (by hand) to lightly chamfer the primer pocket mouth, and that helps. It needs to be done only once, and it doesn't take much time.

I once came into a supply of several hundred WWI .45 ACP REM-UMC GI brass cases. Apparently at that time, the original primers used were somewhat smaller than standard LP diameter, enough so that it was impossible to seat normal LP primers. I had to ream and chamfer all of those, which was a little difficult. It took a lot of reaming.

Breaking the decapping pin should not be a concern