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I know they’re quite different
Three of them are quite similar imo. First split off the Tudor, Explorer, and Railmaster and pick which of those you prefer. Fitting well under a shirt cuff and looking good with a suit as well as a t-shirt would probably guide me.
Then you can just make a relatively objective decision about which goes with what you wear most of the time. and which is the most comfortable. From that list I'd swing towards the Speedmaster as it wears well on different straps and ticks off chronograph from "the list", as it were. Whereas if you've got a DJ do you really want another steel sports watch down the line?
hugo7
JB
Speedmaster First Omega in Space
Tudor Black Bay 36
Rolex DJ 41
Omega Railmaster
Rolex Explorer 1
I know they’re quite different but I like them equally. Not that concerned about holding value - just want a watch that I like. BB36 obviously lowly of the low in comparison to the others but it wears very nicely on my tiny wrists.