I don't know any of my extended family (the only family members I know are my parents), so I haven't had the same experience that you, Locke, and raytri have had. The closest comparison I can make is seeing my late friend the beggar slip into schizophrenic episodes in which he could no longer comprehend what was real and what wasn't. If something like that (but permanent) happens to either or both of my parents, I'm not sure whether I'll be tough enough to take it.
With the disclaimer that I could be entirely wrong, where the soul is concerned, I don't think that time has ultimate meaning, so I think that the souls of all people in God's grace are, ultimately, already in heaven. I think that their only problem is a lack of awareness of where they truly are. That is a rather odd belief, I know. What is most relevant about my philosophy, though, is that I think that in some sense, none of us- including those of us who are supposedly of sound mind- fully understands who or where we really are and that existence is a realization of such things.

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"Some people complain about the system. The system is not good, so they can't do anything. It's an excuse. Freedom is in your heart." (Jin Xing)