Maybe I am not a great negotiator. On a speedy racing model I was only able to get 3% off list at the Omega Boutique AD here.
I feel like anything off at an OB is pretty fair negotiation -- certainly I've never had anything but blank stares when I've given it a whirl. You did well, sir!
I'm not much a flipper or seller, and while I've found some decent deals on the last few Omegas I bought, I liked each of them enough that I'd have been fine spending a few hundred more on each. And let's face it, often whatever's saved on Watch X gets spent on watch Y soon enough, and the whole crazy, magical Circle of Watches begins all over again.
I've been lucky for the most part with my Omegas -- each but one has been a well-made, technically sorted watch that I've really enjoyed, and the one that didn't work out was sold on for pretty much what I paid for it.
Of more concern, for me at least, is what seems an inexorable rise in prices coupled to the "reduced margin/ end of discounts" mantra that I've heard repeatedly in recent trips to ADs, with Tudor now joining that group. When the Omega entry point is above CAD 7k (SMP Diver 300) then the distance between it and, say, a BB58 is starting to look significant, let alone between that SMP and interesting watches from Longines, Oris, Sinn, and so on.
But I guess it's a winning strategy for Omega, based on the scarcity of some models and the value retention of others now.