Sometimes organizations feel pain but they simply suffer through it. The pain isn't enough to justify the risk and effort of making a change. I see this sometimes with my clients and I've learned to be patient. Be patient till either the pain gets larger or the risk and effort get less.
Updating this website fell into the category of pain that I suffered through. But earlier this year Owen introduced me to a new platform for my website. This new platform, called Docusaurus, is easier for me to maintain and should cost me less than half as much to host in Azure. So in this case - the pain didn't increase but the risk and effort was reduced.
Docusaurus has some cool technology under the covers. But for me, the key was that I could write new content (like this blog post) in Markdown. I work with Markdown every single day so I'm quite familiar with it. Now I can add a folder in my local repo, create a new Markdown file in it, push to my remote repo and run my deployment pipeline and Voila! a new blog post on my site.