10/23 EDIT--- Some off the board, a couple added. Nobody said this would be easy.
I deleted the back-story in the interest of space. Further update at or near the bottom of the thread.
I'm going to two watches. I had four, now three with my old GMT sold. I haven't forgotten those watches I wanted, which are still available. I have fretted for a week now on which two I'll keep, or sell one and replace, and I have even contemplated selling them all and starting over, to lessen the regret of cutting the collection in half. I'm going to have one "more expensive" piece and one less, and I'd like them to still provide me a little variety until I'm ready to add on again.
Why tell you all of this? Because it's time to solicit opinions, which are welcome but I reserve that right to follow not at all. I'm still figuring it out. But to get some more input here, with pictures, are some of the pairings I'm considering. I'll be interested to have your feedback. As reference, right now I own a Breguet XXI, Breitling Navi Heritage, and Breitling Headwind. Here we go:
Option 1: Keep Breguet, sell others, buy white steelfish.
(Photo lifted from post by Beyond Man--My apologies, it was done in the name of scientific research)
Option 2: Keep Breguet, buy Opalescent Tudor Tiger Chrono a/k/a Date-tona
Option 3: Sell everything, buy lightly used Rolex GMT-C and white Steelfish--OFF THE LIST
Option 4: Sell all, buy GMT-C and Tudor Tiger--NOPE
Option 5: Keep Headwind, buy IWC Cousteau 2010 with bracelet and rubber--NOT NOW
Option 6: Keep Headwind, buy lightly used Stainless/Platinum Rolex Yachtmaster
Option 7: Sell everything, buy JLC GMT and Tudor Tiger
Option 8: Keep Navi Heritage, buy JLC (Cost issue here, but maaaybe)
Right now I could go either way with the Breguet, again only because I think it's probably not an only or only-other watch, but part of a larger collection. i could hold on though, because I'll add back some time in the future. I think that question is answered tomorrow. There is one other white dial watch that sort of enticed me, a pre-owned Omega Hour Vision. Unique, like the bracelet a lot, but at that point I'd be money ahead to keep the Navi, thought the Hour Vision is a little more subtle. As before, all comments, criticisms, psychoanalyses are welcome. After all, whichever of my watches I decide to sell will soon be coming to a sales board near you.
That's my watch budget for the year totally blown! 
. I would be tempted to keep the Headwind though. If I were a Rolex fan, that Yachmaster has a very nice dial color (seen it up close), but you would have to remove the cyclops, 
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