Might be off topic, but does anyone else dread the outcome of their Linux system after an update?

Not really. I don't really worry about that on most of my system. There is ONE computer where an update is a source of stress, and that's my main gaming computer where I had to setup dualbooting with windows. I learned the hard way that my motherboard implementation of UEFI kinda want windows to be there, otherwise it's very picky into which disk is parsed for EFI boot entries. But beyond that, nah. Laptop, desktop, company servers… just roll the update/upgrade, and the dist-upgrade when needed, fix the updated configs (for servers) and it's good to go. Been this way for the last decade or so.

Worthy of note, I'm on ubuntu LTS (24.04 for now) or Debian stable (for servers), so not exactly outdated (I have the latest nvidia drivers…) but not bleeding edge either. I probably avoid a lot of issues this way.