Upgrading was something on my radar for a bit now, but it was a major one that needed time and effort. The hurdles included the plugins that needed updating along with the time to fix up all the other issues. Craft CMS makes the upgrades fairly painless, but sometimes there are hiccups with the plugins.
Changing gears from Craft, I want to talk about Wordpress. I have worked with Wordpress for years, and have not been the biggest fan. I have used it prior to Craft CMS and have had to program in it since. The most recent developments with wordpress make me know that we need to move away from it. The people that own/manage wordpress have gone off the rails. They have threatened major wordpress companies with lawsuits which has made their whole open source community uneasy. This has made developers scramble to move on from one of the biggest CMS (no where near the best) to find better pastures. Circle back to Craft CMS, they have an ability to easily migrate away from Wordpress.
They had the foresight to make a starter template that has everything you need to move away from wordpress. Not only does it have a script to migrate your data from your current wordpress instance, but it also has a basic template using Tailwind. If you want some JS it has other options like Nuxt. Craft CMS has the ability to build out a custom API, but it also has GraphQL caked in. If you want to go headless (Nuxt, Next et al) then godspeed.
I am excited to be a part of this next chapter that will herald in the downfall of Wordpress (I Hope) and see Craft CMS (headless or not) reign supreme.