As a former Rubyist, I still shake my head at:
- Matz letting things evolve too much on their own since the beginning of Ruby and not carefully adding new features. People made fun of it because there are too many ways of doing things (bloat).
- I think DHH did a great job, but then he let go too much to the wrong people.
- All the Zed stuff, massive changes in Rails in 4.x, then Ember (adapters to well-used frameworks would’ve been so much better), then 7 was just too different.
- Ruby 2.7.7 / poor handling of mac amd arch. This killed it for me.
- MRuby and Crystal.
- When Rails lost a big part of the community to Elixir.