In this episode of The Rails Changelog, DHH and I got to discuss a lot. Among what we covered are:
Kamal,
Rails 8,
Authentication in Rails,
The Rails Foundation & Rails World,
On Writing Software Well,
Delegated Types,
Exiting the Cloud,
SSDs and a lot more!
I've never had problems with upgrades, in fact the latest version of Rails make upgrading a breeze. What Rails app version are you trying to upgrade? Happy to help. Rails also has an upgrade guide that's quite good: https://guides.rubyonrails.org/upgrading_ruby_on_rails.html
And you can use https://railsdiff.org/ to check what you're missing in upgrade apps. Anything other thing that breaks would most like come from another gem, which doesn't make it Rails' fault or Ruby itself, in the case of Ruby, you can track everything to the source to fix it. Ruby keeps a change log diligently. Everything is trackable, at least in my experience.
Rails has matured through the years, I'm convinced it's the right framework for any project if you already know it, you can get by with Hotwire for the FE and not run after React and the rest. Happy to be a Rails dev to be honest.