Looking for my first luxury watch

The Seamaster group is rising ! congrats on the watch, as for the AD or OB I know people who don't mind paying full price take nice selfies at the boutique and walk out like it's nothing, as for me every dollar counts and if I can save a few hundreds and still have the same watch in great condition that's fine for me, I guess to each its own!

Have bought Speed Masters from ADs at 10% discount for a current in-production model and 30% for new old stock (NOS). Biggest advantage of buying from an AD (from my experience) is Omega service center warranty work with no questions asked (had to do this on both NOS Speedys, but both had been in the store for a number if years). Current Omega policy is 5 year warranty. Was able to score a 44mm Planet Planet Ocean from the local AD at 30% discount last month since they were going out if business; got to the store too late to snare the Seamaster Pro 300 (2019). If you are thinking of going grey market and want to pay for Omega service, I had my nephew's 10 year old Seamaster Aqua Terra serviced for $500 which included a 2 year warranty.

Similar experience coming in from Madrid. We declared a few things and the rookie customers guy turns to the more senior to ask what to do. The senior guy basically says that if he wants to fill out a bunch of paper work, go ahead, otherwise it's no big deal. He shrugged and off we went.

As for watches with custums your safest bet if you do happen to buy an expensive one over 10-15k, wear it and the box and all the paperwork have them mail it to yourself , some will do it for free, some will charge you for the shipping , usually they will include little bonuses with the package!