First things first, clever essay. I like how you dig into what are usually unreachable topics, and play around with them like so many chess pieces. It is a difficult question, namely how to address different selves at different times. And as far as I can tell the solution is sound, given all the assumptions. I chuckled when you interpreted fantasy and reminiscence as transfers of value across time and agents.
One thing I didn't get is, what would you expect the equilibrium to be? Is it generally that the person should take the plunge? I can't visualize value in a cross-valuer situation. I may read the post again and see if I can scry an answer (and then add another comment).
Either way, thanks for this stimulating read, I appreciate it.