I think you’re mostly addressing issues of user experience. Let me put it this way, just for sake of simplicity, assume all the system did was keep a set of instructions to be read by your loved ones upon your death. The instructions could be to contact your lawyer for a copy of your will, or to delete your porn hard drive, or to deliver a letter to your child etc. Forgot about estate law and those complications. Forgot whether you think there is a need for this service. Assume that you do. What matters for my purpose is that you need to trust this service to keep your info for longer than you will live, and to make that info available to the people you specified when you die. What would make you trust this system with these all important instructions? How could this company set itself up that will make it certain to deliver its promise?