The insidious urge to fix what ain’t broke has arisen. I’ll probably follow the official documentation, unless someone has a better suggestion.
I’m not running anything unusual and I haven’t done much, if any, “customization”. I update packages maybe a couple of times a week, so they’re current.
Should I go ahead and put myself through this now, or wait until support is dropped and I’m forced?
The upgrade itself is never a problem.
The real problem is when your server is running an old software that breaks after the update.
For example I had an old php/drupal site and it broke after upgrading debian because the upgrade also updated php to a newer version that is not supported by that old version of drupal.