And I've had a bad experience with the grey market which turned me off.
My apologies, I should have included it in OP to make my position more clear. I'm going to copy/paste my response to LX from below:
"I guess the more nuanced point I should be making is Wempe NYC is much better than Jomashop. To contrast my great experience with Wempe, Joma has treated me terribly. I purchased a speedmaster from them which required service after a few months (issue with the keyless works). As part of the service they changed my hesalite crystal. The new hesalite crystal was scratched on smudged on the underside. I didn't notice this immediately and when I did and asked them to remedy the issue they refused. They tried telling me the damage to the inside of the crystal (which cannot be accessed except by removing the case back and movement) was my fault and that I was trying to deceive them. Contrasting that with my story in OP about Wempe, it's a no brainer which I will continue to do business with."
But everyone's situation is different. And things may be different depending on which watch we are talking about.