I'm not sure if it's related but recently (last 2 years-ish?) I've noticed some issue with watching files on macOS. I edit a file but the dev server doesn't pick it up for way longer than it should. It's sometimes faster for me to restart the dev server than wait for it to notice the files changed.
I have not dug deeper into this aside from raising my open file limits and closing some apps I thought might be the culprit (but ended up not being the cause).
It's annoying because it's not consistent. The dev server will work just fine for a while then randomly slow down. It sucks because sometimes I spend a decent amount of time trying to figure out why my change/fix/etc isn't working only to realize I haven't been testing updated code (I made a code change and thought it hot-reloaded but it didn't).
File watching is flaky enough that polling based implementations are a better choice. You can stat tens of thousands of files every second, and easily optimize it to check frequently changes files more often. https://esbuild.github.io/api/#watch