I'm new to Tek but not to Linux, these are just my opinions while I wait for some stuff to happen.
Editors - in Vi all you need to learn is
:q! to get the hell out of there and set Nano as your default (
sudo update-alternatives --set editor /bin/nano ) Its on my list to configure nano with the standard keybindings (for example 'find' is CTRL+W in nano, but that does something else in the majority of other apps..) Lets just accept that Windows has created some expectations for keyboard binds and that they are not the ones that grew up with *nix termianls.
Bash & Fish - you need to understand Bash, but the best shell is Fish (http://fishshell.com/) All my non-priv users have Fish, but all the root or system shells are still Bash. I'm a bit dissapointed that Bash is the default in somerhing Raspbian, its setting kids on the wrong way, but then perhaps there is not enough skill with Fish yet in the external memory?
Pagers - Most is just the best one, sensible keybinds, supports following
update-alternatives --set pager /usr/bin/most after installing the packages. Remember that scrollback and pagers are different things :)
Mosh - doesn't replace SSH, but its an enhancement in that it offers UDP access to a shell and allows reconnection. Check out the Mosh site for platform support. I like being able to wake up my laptop and all the terminals just come back to life.
Byobu - multi-window terminal, like screen but better https://help.ubuntu.com/community/Byobu#Key_Bindings, on a remote system run
byobu-launcher-install but don't use Byobu on your main computer, it'll just end up a nested mess, you've got a graphical session for managing your multiple terms :)
Terminator - multi-pane terminal, Shit+Ctrl+e and Shift+Ctrl+o make splits, and you can set the mouse focus to follow pointer (no click needed) which is nice but care is needed with that.
htop - prettier and better, also likes F-Keys so remember that in Byobu you can Shift+F12 to pass F-keystrokes into the app rather than Byobu itself, or just use keys binds as they are in standard top.
I think that's it, these are things that make my life as a linux user and sysadmin better, I don't know whether it's best to leave new users with the defaults or try to help change what those defaults should be expected to be.