VSCode + Catalina
For the most part, the initial upgrade to macOS Catalina was uneventful; I was caught unaware by the wave of permission requests that greeted me—it was 2 minutes of clicking accept or deny and continuing on with my day (though, how normal users will cope is beyond me... it feels very un-Apple). The two issues I did run into were the need to reconfigure Google Drive (again, a minor 2-minute activity) and trying to get VSCode to work properly. This was a lot more annoying. The initial issue was that Git could not be found—this broke all of source control in VSCode. The fix was to run the following from the terminal:
xcode-select --install
and then restarting VSCode. Once that was fixed, the next issue was that I could no longer sign commits with GPG, which gave a similar issue to the initial Git not being found. The correct fix for VSCode is to add it to the list of Developer Tools, which you can find under Security & Privacy. Once a restart of VSCode was done, everything just worked. I also added Terminal to the list, which stopped autocomplete from Fish Shell from constantly prompting too.