Longines Conquest owner here - I'd rather have the Sinn. I much prefer its no-nonsense, toolish style. The Conquest picks up tons of scratches on the polished areas of the case & bracelet - if that bothers you, avoid. There's also no anti-reflective coating on the crystal whatsoever, but that hasn't really detracted from the wearing experience for me.
The Conquest was my first Swiss watch, and while I still enjoy wearing it, this would be an easy decision to make if I could go back. Especially with Sinn prices in those days! 🤦♂️
No one has mentioned Tag Heuer, so I'll go ahead and do that since we're talking chronographs. The in-house Heuer 02 movement is worth considering: column wheel, vertical clutch, 12 hour timing, and a fantastic 80 hours of power reserve really set it apart from others. COSC-certified in some models. To be fair, I do wish Tag would upgrade it with an anti-magnetic hairspring and COSC-certify as a standard. This movement kind of flies under the radar (perhaps because Tag isn't the most loved brand these days) but I think it's an often overlooked gem. Heuer played a big part in the development of chronographs, and there are some nice models in the Monaco, Carrera and Autavia range.
But don't get me wrong, I'm a big fan of Omega, and in particular their movements. Master chronometer, anti-magnetic, co-axial escapement - what's not to love? I'm not saying the Heuer 02 is on that level, but looking purely from a chronograph perspective, it offers things the entry-level Moonwatch doesn't. And you may have completely written off Tag up to this point, but I'd encourage you to visit an AD or boutique and try on some models, you might be surprised.
If I were buying a Speedmaster today, I'd personally go for hesalite. To me, the sapphire upgrade isn't worth it; I like the aesthetic of the hesalite better (makes a change from all the watches I own with sapphire) and I rarely look at my see-through casebacks. The 321 is great, but expensive. If money weren't a factor I'd take it over the hesalite.
Last thing I'll say is that I personally don't like chronographs that can only time for 30/45/60 minutes, and there are so many these days. It's one of the reasons I really like the chronographs offered by Omega and Tag.
EDIT: I have never missed the sweeping seconds, or even considered it really. The subdial is there after all. And being able to make the "big seconds hand" stop and go on command is much more fun! 😀
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