I pulled this out of your post because it's something I think about a lot of the individual changes. Individually, they generally make sense.
It's just that the sum total of all the individual sensible things is a large mess, getting larger every release.
I first used Python in the 20th century, and have clocked many thousands of hours with it overall. Now I mostly program in Go. (Actually, even after ~7 years part-time professional with Go, I'm not sure which I've used more yet! I may still technically have more time with Python. If I do, though, I'm close to the crossover.) Occasionally, I miss iterators, and with Go getting generics it's probably my #1 ask in Go. Other than that, though... I just can't help but notice that I don't actually miss that many features of Python very often. I miss Haskell features, I sometimes miss Rust features, every once in a while I'll miss something more exotic like an Erlang feature, but I almost never think "gee, I really miss this Python feature". It isn't that I can't see where I'd use them if they exist, I just don't sit there pining for them all the time. I consider this a big data point. I should also point out I'm talking about subconscious inclinations, it's not like I'm setting out and daily disciplining myself to not miss Python features. It's just a thing that happens or doesn't. YMMV. I'm probably more often grateful for a missing Python feature than I'm missing it (e.g., it's actually kinda nice after a certain scale to know what "x.y" does, rather than have to go resolving down an arbitrarily-complicated chain of classes, inheritance, method overrides, etc.).
New in 3.3:
- yield from: I'm okay with this
- PEP 420 / namespace packages: I think this is/was the best compromise, but this remains a fundamentally ugly topic for something that is sort-of necessary to have
- raise from None: This is okay for library code
- __qualname__: It's a mess. It's not like I'm against having it, but this is a corner of the language that practically invites you to hang yourself one way or another.
- importlib: It's better than the previous iteration but this package was and still is a mess. Again, lots of this is due to legacy aka "the other packaging packages".
New in 3.4
- asyncio beta (no coroutine syntax yet): While coroutines are highly useful, asyncio and Python coroutines simply are not good. This is the beginning of the badness.
- pathlib: Ok!
- enum: Ok!
New in 3.5
- async def, await: This is the release that really set colored functions in stone for Python.
- "@" operator: I've never used this once I think, but that's because I don't write math code in Python. If I did, I think I'd like it, so I'm okay with this.
- type hints: Another oof moment
New in 3.6
- f-strings: Yay!
- dict now ordered: Yay!
- async generators and such: Again, I think colored functions are a big blunder, but if you have them, you need this.
- Variable annotations
New in 3.7
- PEP 563: Type annotations can be turned into quoted annotations without a syntactic change through __future__ import.
- contextvars: "thread-locals for coroutines"
- PEP 562: Added the Python 2 misfeature back where Python 2 interpreted __get__ and __set__ on modules
- Typing becomes part of the core language, I think this is when you could start writing things like "list[int]" (instead of "typing.List[int]").
New in 3.8
- := Yuck
- "Positional-only parameters" because the simplified CPython API for defining functions has this, so ... Python code needs that as well? Wot?
- More typing
New in 3.9
- More typing
New in 3.10
- And even more typing
- Pattern matching