"If ain't broke, don't fix it"
1)
I would not recommend upgrading your python version if that's what you mean. If you're talking about pip, I simply do this using python -m pip install --upgrade pip. I do this when there is a message in the console after installing a new package recommending me to update pip.
2)
No, in my opinion, there isn't a need unless there is new functionality in later versions or older functions are deprecated.
3)
If I do decide to update a package, I read through the release notes first (e.g. numpy). Sometimes there will be notes about bug fixes and other patches - this is the main reason for me to upgrade packages. In the case of more popular libraries, there are usually fewer bugs and therefore lesser reasons to need to upgrade.
It is also crucial to ensure that all of your existing functions continue to work in the manner that they did prior to the update. This could cause your whole program to fail.
4)
Again, similar to the first question, in regards to a python versions; I have only just switched to using python 3.10 (I was using 3.7 for a couple of years with no issue). I did this when starting a new project, older existing projects still use 3.7.
Regarding pip; I do this when I get the console message.
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Don't stress too much about packages and updates. Get your programming done and you'll rarely encounter any package/environment issues; in fact, you'll probably encounter more errors if you keep cycling to the newest version of everything.
If you're using a package that is still in development (i.e. take Discord.py 2.0 at the moment), you'll likely need to update regularly, however, you will also face a lot of bugs.
