Wow.TL;DR: Short Answer: Consider your situation and your plan. Look at the costs involved for both options and weigh them out.
Thank you for writing out that “dissertation” .
It honestly is very much appreciated, both to hear your conclusion and simply to know that other people have agonized over this decision as much as I have. I had thought of the “hidden” insurance and registration costs and it definitely all adds up.
I am now heavily leaning towards the new JLU with a mild build over the old Jeep, for now at least. All the comments from those with families really makes me want to share this hobby with the entire family, especially as the kids get older. Nothing to say there can’t be an old project Jeep years down the line in addition the the JLU.