Jessica, is this such an important concept that we may need to embrace even before any other aspect of death and dying. I agree that we currently view death as a failure somehow. Death is the next great adventure - the last frontier so to speak, that we have not yet truly explored. I read somewhere recently that there is a culture in India that celebrates the dying and mourns new birth, which might be interesting to study. You may want to look up sharedcrossing.com as they are trying to change the conversation around death and dying.
I am surprised that my favorite - left their body - is not on the map! For me, I don't use the word dead because I have experienced enough evidence that in some form consciousness survives the loss of our flesh puppet. So the word dead has no meaning for me. It is not descriptive enough. It is definitely not because I don't want to talk about death! I am actually much more interested in talking about it than anyone I can find. :)
I really like the idea of a match.com type of website. Ideally someone requiring support would have a few people in a group (vs just one person), much like 12 step programs where one might have a (main) sponsor and then lots of back up people to talk to. This would help alleviate the stress on the sponsor and make the user more able to have support as and when they need it, despite time zone differences, quantity and types of questions etc.
My two cents on the design by disease etc. In the last five deaths within my family, each one had completely different circumstances and I had completely different needs with each of them. A sponsor and/or support group, where I could have directed my questions, would have been so very much appreciated! For example, my daughter was suddenly in ICU on life support for 9 days. Nine days without sleep and very little access to all the information that I really could have used. I had emotional support from family and friends but no one to help me with questions. Really, dozens and dozens of questions of a variety of type. Perhaps the "sponsor" could also be chosen by type. Or maybe the question gets asked, like reddit, and answered by whomever is available. It would be critical that in some way these volunteers are vetted and verified. I would certainly pay for this as an app. It has been my idea that we need a Death Concierge service as well as more readily available Death Doulas.