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?
How much pain you should expect is easily answered: Expect several things to break and having to do a full reinstall. So back up everything first.
It will probably not happen, but you should always expect the worst (out of the realistic at least…) outcome and be prepared.