Probably 7.70 for calibre.
You might want to update ADE but leave that for later.
For DeDRM, I would suggest downloading
DeDRM 10.0.9 from NoDRM's Github site.
Any plugins that you have installed and need updating will show up in the Updates popup at the bottom of calibre's main window.
You might want to add the ACSM/deACSM plugin to allow you to allow calibre to download the epub from the .ascm file.
If you are not running a 64-bit version of calibre 4.23, you should uninstall calibre (this will not affect your library or settings) before installing 7.7.0.