I did something very similar just recently. I have a calendar event to backup all personal data every 3 months, based on a checklist. I'd always wanted to automate it but every time I tried, it just seemed such a daunting task that I never ended up doing it.

Last time, I figured I'd start going at it gradually. So what I did was I turned the checklist into a bash script, telling me what to do at each step. I also implemented the ones that are easy to automate. The plan is to knock out two or three items each time I do the backup, until it's fully automated.