I love the boxes and paperwork. I keep it all. I rarely buy any pre-owned unless it has original boxes paperwork, accessories, etc. It takes a very rare or vintage watch for me to buy without paper and boxes.
I’m seeing most brands go lower. Even the non-hyped Rolexes. It’s not just the more obscure. You are right though, the more obscure, the quicker they are falling. Some newer Pateks are even at or just under MSP.
I’m a lucky guy. I have a Batman, a Sub, and an Explorer. I do feel very Rolex satisfied. If I were greedy? A white dial milgauss, a Cellini Prince, or, a Tuquoise OP.
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