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Pro
If you want something a little different, check out the Sinn U50 - about $2500 new on bracelet.
https://www.watchbuys.com/store/pc/Sinn-U50-on-Bracelet-p4871.htm
Pro
Need more detail. Dress watch? Dive watch? When do you want to wear it and with what types of outfits? Any preferences for strap type/color or dial color? Automatic, mechanical, or quartz? Do you already own any watches?
Why used - is it just because you think that will be a better value or are you open to new options?
Hmm haven’t thought that far. I’m looking for an all around casual watch. Something like the Tudor black bay. But automatic definitely. Stainless steel band/rubber preferred
Pro
Honestly I’d just recommend the Tudor Black Bay 58. It’s $3800 new on a bracelet which is a bit over your price range, but used ones aren’t really any cheaper so you won’t lose money. It’s a better size and movement than other Black Bay models. This is one of the best values you can get in a modern watch and is very popular as a result.