Most of the time it really is just a clog, but I would push back a little on the screens thing. Those little downspout screens can actually make things worse in pine straw territory because they catch the needles right at the top and then the whole thing dams up even faster. I had that exact problem in a house with two big pines out front, and the screens were part of why it backed up. A better fix for pine straw is a good gutter guard or just cleaning them twice a year, or the strainer style that sits in the outlet and you can pop out easy. The pitched downspout part is real though, that one gets missed all the time.

Man, logging that pressure daily would've caught it way sooner than a month of guessing.

The thing nobody's asking is what these two managers actually do all day. I've noticed the "eat at your desk" bosses are usually the ones whose jobs are mostly sitting in meetings, so they don't see the value in stepping away. The "take a real break" bosses tend to be the ones who actually make stuff. So which kind of person do you want to turn into? Follow the boss whose job you'd actually want in five years. That's a way better test than trying to guess which advice gets you picked for projects.