Not sure if there's anything in particular you need to have to make your experience better. If you run into issues, you'll find the things you need automatically, I think. It's very much a case-by-case thing. For example: I'm quite attached to tmux, but that doesn't mean it'll help you in any meaningful way.

Your saying that you quite like to learn new things about Linux, and in particular terminal stuff, I'd say that going through something that taught me more about Linux than anything else would be good: Install one of the less beginner friendly distros on an old machine (Gentoo, arch, or slackware). And for every command you put in, first read through the man pages (ie man ) to know what it does. If the three distros I mentioned, arch is probably the most popular, and in some ways easiest. Gentoo is fast, and relies on you getting familiar with compiling things from source. Slackware is super easy to install, but getting the system to work in a way that you would call usable takes time. It doesn't really have a package manager (well, you are the package manager), so you'll have to manually resolve dependencies to install the things you need. Configuring the OS is super easy once it all clicks. That's why I credit slackware for teaching me how Linux works. Once it's all set up, it's incredibly stable, and you'll just instantly know where to look to fix any issues, but installing something like VMware, or a proprietary Nvidia driver is a PITA. Don't approach slackware as a desktop distro. Approach it as either a learning experience or something for an old machine to be running a home server on.

Other things you might want to do: learn some bash scripting, check out awk, sed, and grep (honestly, just the basics are enough to make for some really powerful bash scripts). Of course, getopts is a must for scripts, too. Just start with something simple like a backup script. Iterate over the files in a directory, get the hash, check the backup on some driver (Nas or otherwise), and have the script copy over new files, prompt to remove/ignore/archive files on the backup drive that aren't in your directory, and when both the backup and your source dir have the file, compared the hashes, if different, print out the file stats of both and ask the user what to do (overwrite backup, copy backup to file.bak and copy the newer version, or overwrite the old (sync)). That's a useful script to have, and you'll learn a fair few things in the process. Maybe colour-code the output, and once it's working on your system, see what you need to do to make the script POSIX compliant.