Here's an outline of the action plan. Running a 2011 MBA w/ El Capitan. Is what I'm after even possible? I've tried using Automator's pre-made actions as well as its "record what I do" feature and didn't have much luck. These are all actions I do daily, and it's all routine stuff that seems like it should be able to be automated. 1- startup at some set time (say, 4am) 2- open Apple Mail, move messages from a specified IMAP folder into an 'On My Mac' folder 3- empty Mail trash can 4- close Apple Mail 5- run a program called Email Archiver that turns messages in specified 'On My Mac' folder into .PDFs on an external drive (connected via USB) 6- open Apple App Store, download/install updates 7- close App Store 8- open iTunes, download available media, App updates (and potentially back up iOS device(s) via WiFi if it's not asking too much; I don't use iCloud for iOS backups) 9- close iTunes 10- run CCleaner 11- close CCleaner 12- run SuperDuper to backup laptop drive to external HD 13- shut down (SuperDuper offers a 'Shut Down when complete' option so this last step is easy).