+1. Extra-credit if you've heard of cron.

I don't want cronyism in my data storage.

With 16 rounds of ROT13 encryption for safety?

With your own computers and your own encryption in place. Without sending your stuff straight to the NSA.

Can you please explain how I should use this to: 1) Sync the 1Password iPhone app with the desktop app 2) Share cute cat photos with my wife (who uses Windows, and who is not computer-clueless, but is rather commandline-adverse.)

Keep on using Dropbox. If you use all that proprietary, anti-privacy rubbish then you can assume they can access to all your information anyway.

On the bright side, I wouldn't worry too much about the NSA browsing through your cat pics.

Or if you're willing to put in some work you can try something like this https://fak3r.com/2009/09/14/howto-build-your-own-open-sourc...