Twice bitten, thrice shy. Every MacOS upgrade for the past 5+ years has been a bag of hurt: regressions in functionality and stability, annoying "features" like Notification Center and Catalina warning nags, various PITAs on fixing UNIX/dev toolchains, all for little to no benefit. I've stopped upgrading all my machines (other than security updates), unless forced by a mission-critical app or a new machine.
I have similar feelings. On the one hand I would love to check out the new version of MacOS. On the other hand I use my machine for work and can't afford any downtime. I upgraded to Catalina 5-8 months after it was released, mostly because the initial rollout was so rocky (at least according to the articles on HN). Going to keep my eyes peeled for reviews here in the next few weeks. Hopefully this is a more stable re…
The last part is the key: people who have problems usually complain loudly and widely, so there's a huge sampling bias. I've been using and supporting Macs professionally since the 90s. In that time, I've had exactly one case where a day one upgrade broke something — 10.4 shipped with a bug where all NFS exports were read-only — as long as you did a check first to confirm that any commercial software you were using was supporting (e.g. Adobe sometimes had fairly long delays).
There are two common problems you'll see frequently: a system which was already failing will be attributed to the new OS (I've seen people claim it broke their hard drive, when it was really just the first problem which couldn't be excused as a fluke), and people will often say that their system got slow because Spotlight / Photos were reindexing in the background.