These are going to be the easiest to set up and maintain. There's no expectation that you'll use a "command line" or a "package manager", the OS is the OS and when it updates you get a newer version of it. If it works for you, it'll probably keep working. The disadvantage is that it's harder to modify the base OS if you're the sort of person who wants to tinker, or has needs that aren't satisfied by this. (I haven't personally used these, but I've heard good things.)
Fedora Atomic: Just a normal desktop, with various choices of desktop.
Bazzite: A gaming-focused immutable distribution.
AntiX: A Linux distribution for systems with little RAM. This is one of the few remaining distributions that support 32-bit systems and are not planning to drop it. (I haven't used it, but I'm hoping to use an AntiX container for some automated testing in the future.)
Alpine Linux: I don't know much about this one, but it requires very little disk space.
LineageOS: From what I understand, this is Android, but controlled by you instead of Google/your carrier. Probably your best choice if you want to control your phone and don't want to spend any more effort than necessary maintianing it.
postmarketOS: A Linux (not Android) distribution for phones. There are apparently 4 different phone-oriented UIs available, and there's nothing stopping you from running whatever regular Linux software you want.
Arch Linux: I think of this as the OS for people who like to tinker. It's what I personally use, because I like to tinker. Its Wiki is very useful even for people who aren't using Arch. It has a very simple package format. If you know how to build the software you want from the command line, you can probably make a package for it. I personally use yay to manage packages because I see no reason to deal with the AUR myself.
Debian: Old reliable. Reasonably customizable, stable, and not too difficult to maintain. This is likely to be your best choice if you're not covered by one of the others on this list, unless you need proprietary drivers (you probably only do if you have an Nvidia GPU and are playing high-end games). If you need proprietary drivers, I.. guess Fedora is probably fine?
Python Tutorial: How I got started many years ago
Python Standard Library Reference: This page links to information on Python builtins.
Python Module Index: Note that individual modules have predictable url's, like this one for the subprocess module: https://docs.python.org/3/library/subprocess.html. A bit unweildy for typing manually, but you can create a keyword search for it.
KeePass: The password manager I personally use. I don't recommend it. Even for doing everything locally with free software there are probably better choices, but this is familiar to me.
1Password: A commercial password manager. This is what I'd recommend for most people, although I only use it at work.
About your Secret Key: A security feature of 1Password that I find interesting, and that isn't shared by some other commercial password managers. It helps protect data in case a malicious actor gains access to encrypted password databases on 1Password's servers.
Firefox: The web brower I use. The only notable remaining browser engine that isn't based on Google Chrome or WebKit (which Chrome was based on). I would encorage anyone to use it, both because of the problems with monoculture, and because Mozilla Foundation does a much better job of protecting privacy than Google, an advertising company.
uBlock Origin: An ad blocker for Firefox. I recommend everyone use an ad blocker for security reasons (there are plenty of other reasons, but that's the strongest one). Ad networks are where average web users are most likely to encounter hazards like scams or malware, so cutting them off reduces one's risk significantly. This one in particular is so powerful that Google reduced the functionality of Chrome's addon support so it wouldn't work, and uBlock Origin's developers had to make a less-featured version for Google Chrome users.
Keyword searches: A feature that lets you create shortcuts to a particular "search" in your address bar. For example, by default you can type "wp Firefox" in the address bar to find the Wikipedia article for Firefox.
NearlyFreeSpeech: Cheap, minimalist web hosting.
"Static" sites are those that serve the same content to everyone, rather than the server generating the content on the fly. The simplicity of hosting and decreased attack surface are a major advantage of this, compared to something like Wordpress. But, editing HTML by hand is a chore. Static Site Generators automate that part. I've never used one, but here are a few that have been recommended to me: