On Upgrading WordPress
It's the plugins you see. Some of the ones I currently use I really like. And they don't all officially support the new shiny yet. So just wait, or pull the trigger and deal with breakage? Gutenberg aside, any other compelling reason to switch to 5.x yet?
Only the usual – security fixes. I never let any of my WP installations get more than a few days out of date. I've wasted far too much time in the past clearing up after people have got into my server through a hacked WP installation.
Ignore Gutenberg. It's not ready yet. And I'm not sure it'll ever be necessary. Just install the "Classic Editor" plugin before you upgrade and forget about Gutenberg's existence.
Yeah security fixes certainly a worry. I have things set to auto-update for that very reason. And their 5.0.1 patch last month also included updates for 4.9.x. I'll be honest for the life of me I can't find any commitment they've made to keeping 4.9.x patched long term though. Looks like updating to 5.x and just dealing with any fallout better than finding out 3 months from now they abandoned security fixes for 4.9.x.
I've not had any plugin issues with v5, but I don't really use a great many.
I *am* using Gutenberg, but agree that it's not really ready for the big time yet. Too many niggly things. On the otherhand, I do feel that I probably should be using a WYSIWYG editor in 2019.
Yeah I tried Gutenberg for a bit when it was a plugin for 4.x and found it got in my way. I dunno maybe I'll give it another try after they've iterated over it for a couple versions.
I upgraded 3 of the 4 blogs I have to 5.0.3, installing Classic Editor before so I won't be stuck with Gutenberg (Banal Leakage still on 4.9.9 for a while, some due to checking plugins) and it all went smooth and looks normal, at least interface wise.
Compelling reason was security updates, as Dave Cross said above. I can't imagine WordPress 4.9.9 will get another update.