This is in part due to a lack of foresight, but you can run into all sorts of weird issues that you'd never think of, like this one: we have a feature in our REST API that can return lists of items as CSV instead of JSON (yes, I know, it sounds weird). It requires no effort from our backend services; the api proxy takes care of it. Unfortunately, something changed with dict enumeration order between python 2 and 3, and so when we first tried to upgrade, the CSV files being spit out had a new column ordering, which of course would have broken customer code that relied on it.

The string-handling changes, while necessary, are also a bear to deal with. Since python is dynamically typed, you need to work to find all the places where you need to add a ".decode()" or ".encode()". If you don't have excellent test coverage already, you're going to miss some, and it'll be a game of whack-a-mole until you get them all... assuming you have actually gotten them all.