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The beauty of Ruby is that upgrading Ruby versions is not much of an issue most of the time. Most deprecations are also simple to fix.

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I'd disagree with the upgrade from 2.3 to 2.4:

> Though ISO/IEC 30170:2012 doesn’t specify details of the Integer class, Ruby had two visible Integer classes: Fixnum and Bignum. Ruby 2.4 unifies them into Integer. All C extensions which touch the Fixnum or Bignum class need to be fixed.

https://www.ruby-lang.org/en/news/2016/12/25/ruby-2-4-0-rele...

How many C extensions does the average Ruby developer maintain?

The question should be: how many C extensions does the average Ruby developer have in their Gemfile. And my guess would ranging from a few to many.

most of the time :|

anyone remember 1.8 to 1.9 brutal

No. It wasn't that brutal compared to Rails 2 to 3 that was much more painful :-)

But at the time I thought that the transition to 1.9 was handled poorly and took way too long.

Little did I know that Python 2.7 would still be supported today.

hah. try 1.8 -> 1.9 w/ Rails 2-> 3 happening at the same time :))))

I joined a project that did that, luckily I joined by the end, but I could see the toll it had on the other developers.

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