Cory Doctorow put forward an open question:
Open question: when a friend dies, what should her loved ones do with the data on her hard-drives? Assume that she has been using the Internet for more than a decade and has archived email, personal files, etc, on her machine(s), and has not expressed any particular wishes about this data. Assume also that the drives themselves are unencrypted.This is not a new question. People have been forced to figure out what to do with the physical bits somebody leaves behind when they're gone since before written history. Even when dealing with what to do about the non-physical bits the question has been asked elsewhere. How can it not since we've had home computers since the late seventies.
In answer to the actual question, and keeping in mind the limits imposed I'm going to have to be to borrow from one of the boingboing posters.
Allow yourself time to grieve. No really. What you're bout to do is going to be hard enough as is. Give yourself time to let go be it a week, a month, or however long.Online Data is harder to dictate terms to since usually the Terms of Service prohibit sharing account details and have no real provisions for what to do with the bits of You left over. I would personally hope someone like Jason Scott and or the Archive Team would archive those digital scraps of my life before whoever's in charge of the servers decide that they need the space more than a dead man's digital self needs to keep existing, but relying on the good will of others (even when they make it their business to do the sorts of things you would like done, is a chancy gamble.
Anything that has to do with work (freelance or otherwise) should be sent to whoever the intended recipient was supposed to be.
Pictures, Notes, and the like that are left unsorted can be gone through like traditional scrapbooks, belongings, and the like.
Anything hidden please leave alone.
Hard drives and online accounts are the new shoe boxes full of memories people find in the home when a loved one passes away. Remembering people is a way of holding onto that connection you have with them. Being able to share common stories and feelings will help everyone move past a terrible event. If you just destroy all of the data you will one day wonder what was in there.
If you look you might get upset for a moment but destroying all of those memories to avoid your feelings maybe being hurt by something you might discover seems so selfish. You might come to understand them better. All sorts of things can happen, some good some bad but could they be any worse than how losing this person from your life made you feel?