Hi guys. What are the things to lookout for when purchasing a prepared/brand new watches from grey dealers like Brighton’s, Chuan and even Watch Exchange?
What are the “right” questions to ask that’s not condescending in regards to the authenticity and history of the watch like servicing history etc (for preowned watches)?
Just ask them nicely, say that you're new and genuinely concerned about authenticity. A good grey dealer would gladly show you how they authenticate. Building trust and relationships are also part of their job. If any grey dealer takes offense, then just walk away.
I'm not sure how are they going to prove to you (as I've never bought from grey, I go carousell) other than the serial number, and maybe show you a 10x scope of the Rolex logo on the glass. There are many other small nuggets to look out for (google it), but the best is if they will take out the movement to show you the inside of the watch because that's the easiest to spot with an untrained eye.
Also, check thoroughly for scratches/ dings, etc, and make sure you get what you pay for.
Other than that, your best bet is to trust the authenticity and only buy from really reputable shops. If you're feeling paranoid, then make sure your purchase receipt, etc. matches the watch you bought, and you can pay a third-party authenticator to help you double-check.
Somehow going the carousell route can be more assuring as you both will let the uncle inspect fully on the spot before you pay the fella.