If you "have no problem with keeping software up-to-date" then don't complain about these type of changes. As developers we either are responsible about version policies or we're not. Let's take Ruby 1.8.7 as an example:
If you were responsible you went through several patchlevels of Ruby 1.8.7, you're using the latest release (to fix security issues if nothing else) and you had five years to migrate to 1.9 (which most likely meant changing nothing in your code, just testing it).
If you were not responsible and you're running on something different to the latest patchlevel version then you're already running on faulty/unsecure software. Killing support upstream (again, after five years!) is not likely to change whatever you were [not] doing.
PS: Please don't refer to people like the ruby-core team as "cool kids who easily get bored". We all have our biases but name-calling doesn't add anything useful to discussions.