I'll list how got there in roughly chronological order.
Should note, these aren't the only combos I tried, but the ones that best represent the lineage of my thinking.
Thanks for taking the time to share your thought process. I think that's really cool. I don't have access to the same rums otherwise I would try your version in a heartbeat.
My experiments went in a different direction because I went with the Appleton 12 early on and it has plenty of depth. Then it was just a matter of pairing it with a compatible aged agricole. I tried a few and some were surprisingly too tame to add much interest to the drink. I really like it with La Favorite vieux rhum because it is still a bit rough around the edges like a white agricole, and complements the Appleton amazingly well.
I recently bought a bottle of the Clement VSOP based on the recommendation from Rumdood and after trying it at Tiki Oasis. Also I had a chance to try his version of the Mai Tai at 320 Main a few times and it is quite good. (They use Clement VSOP + Appleton Reserve + Clement creole shrubb.) But I haven't had a chance to crack open the bottle of Clement yet.