In the old days digital inheritance was simple.
Say I died in 1999. (BTW, I don't expect to this for decades). Back then my computer was owned by me and it would have passed to my estate . Where the computer goes, so goes its drive and data  including tax returns, photos videos,, Financial records, password stores and so on. 
Those were the good old days. In 2013 we know that DRM'd media, like software, dies with its owner ...
... this piece of prose from Apple’s legal department says this about apps:
You may not rent, lease, lend, sell, transfer, redistribute, or sublicense the Licensed Application and, if you sell your Mac Computer or iOS Device to a third party, you must remove the Licensed Application from the Mac Computer or iOS Device before doing so.
I’ve scoured Apple’s iTunes Store Terms and Conditions documentation and I haven’t found verbiage specific to movies, music, audiobooks, and e-books, but I’m assuming these same restrictions apply to those media flavors. Given that, Apple seems to be well within its rights to say that when you expire, so too does your purchased media....
So what about the Cloud? What happens when all of the family records and documents and passwords and photos are stored in Dropbox or Google Drive or iCloud? Can Facebook records be downloaded by the estate? Do access rights go through probate?
Wikipedia has a short article ... (emphases mine) ...
... Gmail and Hotmail allow the email accounts of the deceased to be accessed, provided certain requirements are met. Yahoo! Mail will not provide access, citing the No Right of Survivorship and Non-Transferability clause in the Yahoo! terms of service...
... Facebook's policy on death is to turn the deceased user's profile into a memorial... no one is able to log into the account in the future...
American states are starting to make laws with a focus on Facebook ...
Now, lawmakers in at least two states — Nebraska and Oregon — are considering legislation that would require social networks like Facebook to grant loved ones access to the accounts of family members who have died.
Oklahoma passed a similar law in 2010.
"We have automatically vested in the administrator of an estate the power to act on the behalf of a deceased individual and access these accounts," Ryan Kiesel, a former Democratic legislator who wrote Oklahoma's law, tells Morning Edition host David Greene. "That's not something they have to go to court for. They have that power, just as they have the power to pay debts, to distribute property according to a statute or according to a will. One of their powers in Oklahoma now is to be able to access these online accounts."
Yes, Oklahoma is a technology leader. Surprised me. 
Dropbox is clear that content is owned by the account owner, but I couldn't find any references to estate access. Google had nothing on Google Drive, but they do provide access to Gmail. On iCloud I found nothing at all.
 The software is licensed to an individual though, and, technically, is not inherited. That's precedent for the bigger problem.
 In fact it's family property, but I'm simplifying.
 Back then we didn't encrypt hard drives or backups btw.
 I'm going to ask my MN state representative to have a look at this post.
Update 4/19/2014: Google has added “Inactive Account Manager” settings to Google.com/settings. It’s under the Data Tools menu currently. You can choose up to 10 trusted people who will be notified when primary account is inactive for at least 3 months - you can set range to 18 months. You have to specify a phone number that will be used to notify the recipient, so there’s a risk that number will not work when needed.
I set this up on my primary account. When i first configured it I was able to specify what went with my account, but afterwords I couldn’t see those choices. I think that’s a bug or a missing feature.