Would say it's definitely possible. They already do the Speedmaster in 38mm and they could be looking over at the Breitling SuperOcean in 36mm (targeted mostly towards women I believe) and want to capture that same market/target demo. Also, I believe the watch trend is shifting a bit now to watches on the smaller side, compared to the oversized trend of a few years ago.
My first watch was a Casio Baby-G that my parents got me in grade school. Since then I'd always wear a watch, but I think the fascination and spending hours on forums and watch YouTube started after I got my first automatic, Seiko 5 SNKL43. Now also own a Timex GMT, Seiko tank and vintage Omega Seamaster. Am taking a bit of a break though and hoping to save up for a piece or two in the luxury tier (still love my affordables though).
This is a fair point, but I think when it comes to selling pre-owned, your local market plays a huge role in how easy this will be (assuming you are selling to strangers and not to someone you know/friend of a friend situation). The market for watches in my country is not big, maybe I could make my money back on a Rolex, but an Omega or a Tag may be a different story (also have to consider how long I'd be willing to wait for someone to give me the price I want). I could try sell internationally but buyers may find that with shipping + import tax, it's not worth it. I could sell to a secondhand dealer locally but I definitely wouldn't make my money back since they dealer needs to make money when they eventually sell it. There's also a fair bit of admin involved when selling anything deemed "expensive" - I'd expect quite a bit of back and forth, so if you're a busy individual, the time you'll spend in correspondence (and the person you're talking to may end up deciding not to buy) may not be worth it to you.
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