A big part of 3 was Unicode strings. In 2 you could mark a string as Unicode with a u””. This would have been a great way to let libraries and code work with both 2 and 3. They banned this, but you had to still use b””. This was the attitude and just one example.
The list of stuff that got hard / slow was long. Migration path was unnecessarily difficult as was compatible code. Somewhere around 3.4 it was like a light switch flipped and they started being more reasonable. ASCII handling improved (yes, not all internet protocol stuff is Unicode), they began making it easier to target 2/3 etc. but it was horrible to start. I’ve thankfully forgotten some of the details :)