There was some pain around Ruby 1.8->1.9 because of string encodings, but no huge schism ala Python 2/3.
Did you experience both transitions or is that just your feeling based on this article? If anything, I think the article proves how relatively painless the transition was.
I know, and help maintain, Ruby code written for 1.8 that hasn't been touched and is running fine in 3.2. No breakage along the way.
To be fair, that's not always possible, but Ruby's changes haven't ever been drastic.
I've not had as much experience with Python as a programmer - more as a user of apps written in Python, and I sense there's a bigger issue there than Ruby has ever had. It seems like a frequent problem that something that works in Python 3 doesn't work with Python 2 and vice versa.