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?
I’ve found that dist upgrades themselves are fine, but it usually breaks something. Last time it was my janky WordPress installation which was using PHP 7.4. The wordpress version was up to date but it wouldn’t use the installed 8.2 php and just broke. In the end I installed a fresh wordpress and copied the data over.
The trick is to get wordpress from debian’s repos itself. That way your wordpress is managed by debian and receives automatic security updates.