At DrupalCon Pittsburgh 2023's Higher Education Industry Summit, WCMS lead developer Kevin Paxman presented "1000 battles, 1000 victories: The process of moving 1000+ University sites out of Drupal 7".
The 15 minute presentation, which did not really cover all 1000 battles, touched on some of the history of the WCMS, technical decisions that were made, how the profile was built, problems that were encountered along the way, and more. There were slides on things we could have talked about if we had more time, and all the things we have to talk about in the future, but ironically there wasn't enough time to go over these slides in the live presentation.
The talk was not recorded, because it was during the summit and not "DrupalCon proper", but other recordings from this and past conferences are available on the Drupal Association's YouTube page.
Below, you will find a copy of the presentation in PowerPoint format. Blue text in the presentation is text that was intended to be skipped over for time purposes, provided for the quick readers in the crowd.
DrupalCon group photo
Additional photos can be seen in the Conference Flickr pool.