This has always been inconvenient for those left behind, but in the digital age it's a particularly inconvenient. We don't use biometric authentication yet, but user names, passwords and the locations of things are bad enough. (Imagine when we do biometrics...).
So how does one communicate this key information 'from the other side'? What method is most likely to work? Where should the information be stored and how should it be shared?
After playing around with a few options I've settled on a basic Google Doc that is shared with my wife , my brother, our executor, and several relatives and friends. We all use Google, and I assume access to a shared document will survive my demise. As a document of course it's simple to print a paper or PDF version that can go with our will. The paper version will include the URL of the shared Google Doc and directions on how to access it -- the paper version is a backup. This isn't a legally binding document but it's advisory so it's good to know the "source of truth" and it's handy to be able to see all prior versions and edits over time.
As a shared document it's somewhat private, but potentially public. It won't hold any truly confidential information.
Since it's a Google Doc there will be a synchronized copy on my Google Drive; a copy whose name, at least, is Spotlight indexed. The information is fairly robust -- anything that would take out all copies of the documents for all users would probably make my estate irrelevant.
Lastly, but not leastly , it's easy for me to edit. So I can put together an outline and gradually fill in the bits as I think of them. Odds are I'll get thirty years to work on it.
But you never know.
Here's the current outline, I'm sure it will expand.
- Metadata: Title, author, last revised.
- About: Describes use, includes URL on Google.
- Passwords and Combinations: Where my 1Password archive is and how to get to it -- including the location of a backup copy of the global password (paper). Where I keep the simple household combinations.
- Backups: Where my backups are (office and home) in case of need.
- Money: Where the money is. This is most important if both Emily and I are taken out by an errant meteoroid.
- Domains: I own about a dozen domain names. Some are worth money, some provide access to digital content the kids might want.
- Photo archive: How to get the family pictures.
- Media archive: Probably not a top priority, but no reason the tunes should go.
- Kateva: Dogs don't get into wills, but executors look for advice on canine provisions. I suppose I'll say something about the gerbil too.
- What goes to which kid: This is the dangerous part. Who gets the Family domain? Who gets the wedding ring? (Ok, the last one is easy, we have only 1 daughter.) It is something I need to do though.
- Dispensing of "John Gordon" (not my TrueName) - including the blogs.
 That really should be a word.
 Once it's setup I'll make her 'owner' and I'll keep edit privileges. Helps with survivorship. She can do the same for me of course.
 Almost impossible to type. Since the data isn't super-secure I used Google's URL shortening service to create something one could read off a paper version and type in a browser.
- Gordon's Notes: You're 50 now. It's time to start plan 0. 7/2012 - it's a cheery time of life :-).
As I worked on this my outline grew. I also realized, with mild horror, that if the server were lost or destroyed my estate would need the passwords to my encrypted offsite backups. "Best" security practices are hell on an Estate. For example -- Google two factor. What if my phone is gone too?!