Based on my personal experience with two CZ pistols (TSO, limited-edition 75) and a bunch of Glock and Sig service pistols, your Shadow is going to be far less tolerant of out-of-spec cartridges than your Glocks. The latter are designed, first and foremost, to be reliable, so they'll happily eat cartridges that are likely to badly jam your Shadow.
My sole source of 9mm reloading brass is what I hoover up from the range, so it can be anything from once-fired quality brass to cases so beat up t's hard to read the headstamp. Firing cases, especially repeatedly as reloads, in service pistols expands the web past SAAMI spec, and your Dillon won't resize the case web (nor will any other press/die combo short of commercial roller dies). In my painful experience, it's these cases that can cause the hardest-to-clear jams.
Do yourself a huge favor and get yourself a Wilson case gauge and test every round that comes off your new 550 (mine's almost 25 years old). Reloads that don't cleanly drop into it should be put into a "Glock jar." I also mark those rounds with a sharpie so, if I pick them up again after a range session, I dump them into the recycle bin.
Edit: I've also found my CZ chamber throats to be shorter than the Glocks, so rounds that chamber cleanly in the Glocks might jam the bullet into the lands in the CZ.
