I still have battlescars from capistrano. What a pain. So much easier with docker.
I remember trying to solve silly problems:
- productions servers should not have C compiler installed (why???) - compiling assets on every single VM that runs service is twice as silly
I'd still take that over something like AWS Beanstalk.
The issue is how much RoR does and how tightly it is with its build toolchain - gems often require ways of building C code, whatever you use to build assets has its own set of requirements, there is often ffmpeg or imagemagik dependency. In my opinion, a lot of the issues are from Ruby itself being Ruby.
I agree that it's silly for such productive framework to be such PITA to deploy. To be fair, I pick RoR deployment over node.js deployment any day. I still not sure how to package TS projects correctly.