Perhaps before diving (pun intended) into the intricacies of various models, ask yourself what you want out of the watch first. Would you enjoy a chronograph, take it swimming, automatic vs manual winding? What about size of the watch?
I see that an Omega Speedmaster is missing from your list. Have you already ruled those out or have not yet looked at them? There are options for a couple different sizes as well as movements. Both automatic and manual wind. An absolutely kick ass classic model that will stand the test of time. Brand new may be stretching your price range but pre-owned is very doable.
I would suggest looking up
@WatchVaultNYC and his current offerings. He's highly trusted on this forum and well worth contacting.
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