I'm a big fan of XFCE for your DE/WM. It allows you to set loads of keyboard shortcuts for various WM activities like launching programs, switching workspaces, moving/resizing windows. As far as non-WM activities, look elsewhere in this thread for program recommendations.
The only Linux distro I can stand is Arch Linux. It will require you to become a sysadmin (comfortable with a shell, editing a few config files here and there, and following instructions from the wiki), but you sound comfortable with that. Arch will never break beyond recovery for you. It's a very simple distro that doesn't try to "do everything" on your behalf. Other distros like Ubuntu, Mint, and Fedora all seem to have a significant chance of self-destructing when I update them. Arch just keeps working. I've been using it exclusively for over 7 years.
The only Linux distro I can stand is Arch Linux. It will require you to become a sysadmin (comfortable with a shell, editing a few config files here and there, and following instructions from the wiki), but you sound comfortable with that. Arch will never break beyond recovery for you. It's a very simple distro that doesn't try to "do everything" on your behalf. Other distros like Ubuntu, Mint, and Fedora all seem to have a significant chance of self-destructing when I update them. Arch just keeps working. I've been using it exclusively for over 7 years.