1. I use Foreman to land Env variables from a .env file which is not part of the repo. So no sensitive data will be stored in Git
2. UU years, I think 2 years, where last month I finally had the time to make VirtualBox the way I wanted it to work - never had the time to sit down few days and just do it.
3. Docker, I honestly recommend their documentation it is so well written and to the point that you will need just 2 weekends to know all you need. Very impressive. But sure, I'm might do an update on that :)
4. About the encrypted disc images, they are in the iCloud folder, so they are bucked up there, and are encrypted on their own so I don't care even if someone would get access to my iCloud account.
Hope this helps :)