I have been running my site on Plone for a long time, but the maintenance required was too high and I ran into several issues with bloated data file, unsupported plugins to name a few. Plus the instance was not very portable in case my server died or I had to move.
Then I was thinking about creating my own content management system, but time was a factor and the I thought I was losing my focus. What do I really want to do? Publish my thoughts, or develop something new. Actually it is both, but I don't want it to become dependent on each other. So I decided to use prebuilt software. I very quickly evaluated Drupal, WordPress, Movable Type and decided that WordPress looks to be the best at this time. More on the evaluation later.
Second challenge was to make it completely portable by using containers and not just VMs.
To be continued...