Here is my long winded opinion:
It really depends on A) the AD and B) your negotiating skills. There are many ADs who simply will not go more than 10% off or some other arbitrary discount. That's fine, take your money elsewhere. When I bought my DJII right when they were released I got it for considerably cheaper than any grey dealer. I also got to try on 5 or 6 different DJIIs in the store and decide. The dealer also sized it for me and I enjoyed supporting a local business run by a watch enthusiast.
I just bought an Audemars Piguet that was priced lower than 90% of grey dealers and was matched with the lowest grey dealer I could find. On a nearly $21,000 list price watch, it was worth the peace of mind to purchase from an actual AD with my name in the warranty booklet. The dealer also has a relationship with AP and ordered a strap for me that a grey dealer likely would not be able to do.
On the other side of the coin, I bought my Panerai on the grey market for nearly dealer cost. It was a few hundred cheaper than any other grey dealer. I never needed the warranty, but now that I'm a better negotiator I probably could've gotten a similar price at an AD I now have a relationship with.
I think if you want a watch *now* and you'd rather not negotiate, grey dealers are a good fit. However, it's worth a little extra time to me to find good ADs that I can build a relationship with and know I can count on in case there are any issues with my purchase.
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