If you really want to go diving underwater, get the diver. (d'oh!) If WR is not really an issue (150m for the Railmaster is more than enough for everyday use), I'd say maybe get the slightly more boring/understated watch. Why? Because gimmicks can become tiring, and you want something for the long haul.
I'd say Railmaster, because 1) it feels more elegant/understated, can be dressed up/down and 2) I can't stand the 300m diver. Hurts my eyes every time, but it's just me.
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