You having regrets depends on your expectations. If you want a very stable system with little maintenance then you’ll be happy. Packages will be older but that’s what makes it easy to keep stable.
I’m not personally a fan of vanilla Debian because the stable versions are a bit too outdated for the things I like to work with. I do use Debian derivatives though the LTS versions.
I knew someone who did this but swapped out the physical hard drive each time. I wouldn’t dual boot because then it’s much more obvious to IT what you’ve done.
This is only realistically feasible though if the hard drive is easily accessible. If it’s something like a Mac or soldered in dual booting is your only choice. As others have said, this could get you in a lot of trouble with your company. Check the docs you’ve signed
It shouldn’t break if you just install packages from the main app installer. It’s more of a concern if you’re trying to install anything from source.
Also make sure to try a live cd or live USB to make sure the OS is compatible with your hardware. VM is not sufficient for this last one. This is usually only an issue if you have very new hardware.
I would get comfortable with the idea of breaking things. Make regular backups of your data. The best that I’m aware of for making it easy to work backwards from breaking things is NixOS, but I wouldn’t consider it beginner friendly.
You learn a lot from trying to bring a system back online. But it depends if you’re trying Linux to learn it more or just to take advance of privacy.
Yes, though this is true of a lot of the easier distros.
I was newish to Linux and had just run rm -rf ./.* to remove all the hidden files/dirs in a directory. I then wanted to run rm -rf ./* to clear the rest, but I accidentally ran rm -rf . /*. By the time I noticed it was taking too long and hit Ctrl+C, it was too late.
What IT guys did you go to?
It’s WAY better than batch (not to be confused with bash) scripting. It’s got some really nice features though and lacks a lot of the small paper cuts inherited from legacy shells. Look at nushell for something similar on Linux.
You didn’t get any instructions before hand? Is this in higher education or earlier?