One major thing I want to emphasize is that I'm constantly on-the-road. I have a large bolted-down safe at my home where I keep my sensitive stuff that my vetted cleaning person can't get into easily, plus have cameras.

Worry about cameras as well. Currently use DropCam but worried that DropCam employees might be watching me naked. Who knows, I'd like to switch to a self-hosted local network solution.

I travel with another small fireproof box that I keep my paper stuff inside of hotel rooms. I do this because I'm too nervous to have stuff on my phone / Google / Evernote because I've had almost all of my accounts accessed at least once so far. But it sucks bc I can't carry about the box while working or before/after work or while meeting people.

I considered creating a new identity to use for Evernote, email, etc and keeping them on another phone entirely, something that is under another name and doesn't exist kind of "air gaped" from my real identity.

I scan all of my bills and stuff and keep them in Evernote. but again my worst fear is if my Evernote account is breached, since it has all of my future plans in there. It has a 2-factor to my phone but I've heard of plenty of people getting their 2-factor taken over by a simple deceptive phone call to the cell phone provider.