Ive never done that and ive never had a problem. If youve got only one watch with you, receipts definitely sound like overkill, especially if its on your wrist.

Having said that, I have a funny story from a year or two ago when traveling to Canada.
I was alone, so they singled me out to search my luggage. I was wearing a Skyland, and the officer asked me about it. I told him that I bought it in LA. He asked me how much it cost etc. He didnt seem to believe me, but whatever... So he takes my laptop, turns it on, and starts looking through my files. Im not sure how legal that is, but I didnt want to rock the boat. Whats on here? my files. Any pornography? Probably. While in there, he finds the breitlingsource pricelist. He gets all excited and starts questioning me about why I have it. I explain what it is. Again, he doesnt seem to believe me. Eventually he doesnt find anything else and says im free to go. Being inquisitive, I ask him why he was making such a big deal out of it. He admitted to me that he thought I was smuggling watches across the border and that the pricelist was some kind of database of my prices and customers lol..

I travel out of the country frequently. Never had a single issue with watches, jewelry, designer items, or computers, either brought or bought. In fact I often purchase things while there, fill out the duty free forms, present them at customs, show the items purchased, and the receipts, along with your passport, get a customs stamp, at the airport, all in the country of origin. Proceed to the duty free stations, also in the airport of origin, submit the paperwork for a refund, get on the plane and go home. When arriving back in the States, fill out a customs form, write down the purchases in generic fashion, (jewelry, hand bag, shirts, etc., failure to declare may result in forfeiture) along with the approximate amount, (discounted, maximum personal exemption is $800), pass through customs and go on your merry way. I've been traveling abroad for almost twenty years, been to some not so popular places, as well as tourist hot spots, and I've been singled out for additional bag screening 2 or 3 times, in all that time, without issue. Nowadays, US Customs and Homeland Security have their hands full with bigger issues. Do you really think they are looking for a guy that bought a watch duty free so they can collect a hundred bucks? God I hope not! The biggest issue I've ever had, in fact, was also Canada. I travel out to Edmonton half a dozen times a year and have been singled out for extra scrutiny a few times. Not for customs declaration issues but for immigration issues. As a result of the oil boom up there, foreign workers try to get into the country to work without the proper clearances. I often have to prove I'm there on approved business, with a short duration stay and they let me pass.

(disclaimer)
Hopefully I haven't cursed myself and anyone taking my advice does so at their own peril.

Good to know and yes, I agree with much you stated!
I will be on my honeymoon this coming September in St. Lucia and I wanted to bring my (soon to arrive) Navi World along with my CE. (I figured I would have a "day watch" and a nice "night watch")I wanted to see everyones thoughts on this before I did something wrong. This also got me thinking...when bringing multiple watches, do you tend to wear the more expensive one on your wrist?

I agree it may seem overkill and that the CBP has their hands full with bigger fish to fry, but I try to avoid dealing with "Murphy's Law" as much as possible. My situation is a tad different as I work in Iraq and don't go back home but about every 6 months or so. I have a number of watches that roll with me when I make the journey to and fro. The last thing I want to deal with is being hassled coming back home.

I just check through my full 12 watch winder at the luggage counter. What could possibly go wrong?