This all feels like it's trying to apply the web-SAAS model to a domain where it really doesn't fit.
I'd rather have a simple system where I could take any data, easily encrypt it on the client-side, and put it somewhere that's going to stay around for a long time (S3? thumb drive?). Then I give my lawyer the password and instructions on how to use it, on a sheet of paper. At any point, I can upload new data, replacing the old data. Digital security isn't as important because it's always encrypted before it leaves my desk. I don't need to maintain Trusted Friends because the only person with the password is my lawyer, who keeps it with my will.
Dealing with my possessions after my death is a solved problem. It's possible to simplify parts of it, but we shouldn't try to replace it entirely with another model that discards the good parts of what we have.