no you aren't overthinking. It is a good idea to check them every time after you size them. Try to get them about .010 under max or less to keep your carbon ring minimal. They may not need trimming every time but they do need to be checked every time. As long as they are under you are good. If you let them get over the chamber can act as a crimp die and a carbon ring would add to the issue and if you are close to max pressure it could cause a spike for you.
Hey chase check out little crow works. My uncle (60+ years reloading) talked me into one several years back. I plug it into a drill press and hammer out a big batch. I have a couple other trimmers but use this for brass that I shoot a lot. I have the WFT2 and housings for 6.5 CM, 6.5 G, 223, and a couple others.