I just finished delivering my CMS Philly How I am migrating JeffGeerling.com from Drupal 7 to Drupal 8 presentation, which summarizes the first 100 days (1-2 hours per week) migrating this website from D7 to D8.
The slides are available from SlideShare:
And every episode from the live stream series following my progress is available here: Migrating JeffGeerling.com from Drupal 7 to Drupal 8 - How-to video series