That's not a very fair comparison. Python is 25 years old and this migration is being requested after 20 years in existence. There is no way a successful language can perform this kind of migration at that age without pain. Swift will be no exception if it's still around and popular in 20 years.
https://news.ycombinator.com/item?id=7581434
A decade long conversion is fine if that is what the community wants. There are certain drawbacks to this.
I simply like the aggressiveness that Apple has taken. The community can put "all its wood behind one arrow".
Python 2.x keeps working pretty well for many large backend-service codebases that need a lot of stability.
Swift 2.x is used for iOS and macOS client/UI apps that get significant UI "enhancements" every year. The stability desire is much less, in every sense.
Apple wrote a decent conversion tool for 2.x -> 3.x; yes it is far from perfect.
Btw, I documented most of my changes on my blog, in the hopes that the next person would be able to make their changes in half the time:
https://h4labs.wordpress.com/2016/09/17/my-ios-10-and-swift-...
Everyone using Swift will soon be on version 3.x. Compare this to languages like Python where there will need to be a major 2020 conversion to 3.x because many developers are dragging their feet.
The community needs to accept a little pain or pay for past language design mistakes for decades.