Value retention

[Hawkeye1]

One of the main reasons people by Rolex is that they hold their value better than most brands. That said, when one purchases one on the secondary market and pay the premium, you're pretty much committed to that watch because the second you sell it, you're most likely going to take a loss. I'm in a constant struggle with instant gratification and common sense. Reading the Maui post below, I want to fly there tomorrow to buy $10k in jewelry so I can get that Sky Dweller!
In people's experience, do gray market prices hold up over time?