What a collection! I tell myself to stop, but seeing your collection is making me want more!
I have such similar story as yours but only many years later. First got into Rolex in 2012 and never thought I was going to get another one. Some time in 2017 I watched an episode of Hodinkee Talking Watches with John Mayer where he talked about the non-Paul Newman Daytona 6263 and I was immediately hooked by its aesthetics. Sadly at the time a pre-owned would cost at least $30K. Lo and behold the 116500LN came out, it resembled the 6263 so much and became my instant grail.
Walked into many ADs to asked to buy one only to be brushed off/laughed at, I had no idea that a watch could be that difficult to get. Got angry/impatient and went grey and never looked back.
My wrist is on the smaller side so I love the Daytona on my wrist. Till this day it is still my favorite out of what I've acquired so far (along with the Batman).