> I didn’t really trust file encryption because I thought I might lose files because of it and therefore I never enabled Mac OSX’s built-in FileVault hard drive encryption. I should have though. It’d save me from worrying about who’s going through all my files now.
This is a no brainer. I have yet to notice any real performance hit for enabling full disk encryption. Just enable it, make sure to have a long/strong password, and make sure your computer actually locks when you close the lid.
You should never be worried about losing files on a single computer. If they're important then they should be backed up to multiple computers/drives/services. If you're worried about accidentally wiping your laptop when you setup FDE then just make a backup before hand.
> My backup drive was literally NEXT to my MacBook. By sheer luck, I had just backed up my internal drive the day before and they didn’t take it.
Offsite backups are a must. It can be your own "offsite" (ie. a server at friends/parents/office) but it needs to be somewhere other than the primary site.
> I didn’t have a cloud backup because I don’t trust a third party with my data.
There's nothing wrong with not trusting third parties but that's exactly what encryption is for. Encrypt your data locally and then you can store it remotely without worrying about it being accessible to a third party. DIY scripting with GPG/S3 works well for a lot of situations. Or you can just use Tarsnap[1].
Honestly it makes a lot of sense to do the same with USB drives as well. My Linux machine is my primary computer (OS X laptop when roaming...) so the majority of my backup USB drive usage is done there. I have them setup with LUKS/dm-crypt[2] for full disk encryption. It's really easy to setup, plug-n-play on modern systems, and it almost falls into the "no reason not too" category. I just wish OS X supported it too.