Steve, these two aren't comparable.
As to icons, Rolex has far too many to mention, eh? ;) As to the Explorer and the Speedy, apples and oranges. Both are iconic, yes, with the EXP line up being among the very best there is. As to "the" Iconic Chrono, that would be the Breitling Navitimer in my opinion. That said, when it comes to Omega, their Speedy is an icon in its own right, too (though the marketing hype/LEs, well, let's not go there; they're hardly the only one as discussed on your other thread). If comparing Rolex chrono as in the Daytona, ...
Yes, Swiss-made is expensive; it's an expensive place to live and wages are tied to the cost-of-living, etc. , such that for some watchmakers who actually like Rolex make most things in-house as opposed to (cough, cough) outsourcing, prices as compared to those who don't are in turn justified, in my op. (Note: if one wants Swiss made and in-house, there's a corresponding cost to that in turn). If that's not so important, then there's tons of other options out there, no shortage in fact. All depends on what one wants, as don't really need a watch to tell the time (and not the reason why most people buy a "good" watch anyway; just saying).
As per your other thread, I like the Speedy in it's own right, serves a different "itch" (OK, so I'm also a Star Trek fan, too; what can I say, different watches speak to me for different reasons, and probably reason why I can't ever see myself ever having just one ... lol). As to date/no date doesn't matter to me; when I get up in the morning, before I go to bed at night, really, the date doesn't change ... Hence, one of each, both nice, but not really comparable, at all.