For me, the dressier watches have a hard time competing for my money because, frankly, I do not dress up except for weddings and funerals, and i already have 2 vintage watches for those occasions. The tool watches are much more useful to me. Vintage Seamasters are great, but the newer ones do very little for me. I have a relatively new PO, but rarely wear it as it's a bit blingy and a bit too thick. And the Seamaster LEs are haven't caught my attention until the 60th Anniversary model. Also, when it comes to vintage Seamasters, they seem to pop up for sale a lot less often then vintage Speedmasters, so there are a lot less threads dissecting the for sale ads.
The Speedmasters are in the sweet spot for me. Not initially, but after I already had the PO -- until that point I figured I would focus on diving watches (I also have a Sinn UX). But I picked up a '67 Speedmaster and a TinTin, and really enjoyed wearing them due to the size and how they sit on my wrist. Plus the chrono is useful.
There are definitely other brands that catch my eye, but right now it's enough trying to learn all the Omega info, so I have avoided the world of Heuers, UGs, etc. Maybe at some point down the road, especially when there are more discretionary funds to play around with.
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