I switched to Linux a few years back and do the same routine. "I don't use Outlook so I don't really can tell. Sorry". But then they get all clever and say "Here, let me show you" and grab my mouse (which is left handed for starters) and go "...errr... your Windows looks strange". And I go "Strange, or better?" and they leave confused and call the real PC-support.
Here's what I do.
Nightly (my data do not change that frequently) I backup important directories to another drive (used to be internal but is now an external 1TB disk). I have set rdiff-backup to keep 30 days worth of backwards diffs. I weekly mirror the latest copy to an off-site disk which happens to be connected to my workstation at work as they don't mind. I do not mirror the backwards diffs that rdiff-backup use to get old revisions of files.
This gives me screwup protection up to 30 days and theft/fire protection of the current data. The disk at work is encrypted. I thought of encrypting the external 1TB disk at home too but the disk of not being able to restore the primary backup outweighs the protection from datatheft if the disk should be stolen in a break-in.
No matter what backup software or script you use to backup your files see to it that you can go back at least a couple of revisions to be able to recover from the most common source of data corruption... you.
Disks are pretty cheap these days. Some might argue that the space needed for backups are too much, as much as the data you are backing up. Yes it often does but it's worth it. Once you have lost a great amount of files in a screwup or disk failure you gladly pay the price for an extra disk.
Now if I only could find a very user-friendly backup software for Windows that gives rdiff-backup functionality and is also wallet-friendly I could convince my father to start backing up his data.
It is much harder to find a job than to keep one.