Check archlinux.org before updating to see if anything requires manual intervention
informant
in the AUR can also be used to halt updates and automatically show you messages from the site. Then you can just run the update again and it will go through.
I always prescribe learning Python over basically any other language (unless you're gonna start doing some real low-level computing). It's a much more relevant and popular language. C# isn't irrelevant, you'll just see Python used way more often. Python will also compliment JS much more.