When I was writing the question, I was also visualizing my answer, which -- for the first question -- would have been one of the TAG-Heuer re-issues. Since Allen will be at the track with his Monaco, I will take another approach --
How about one of these, as the ultimate "tool watch" . . . you gonna' make me buy a modern watch to take to the races? fine, I'll take one of these . . . at least it will be useful during the weekend of racing!!
In terms of the second question, I have an idea, but I want to think about it. One thing for sure: now that Seinfeld, and a couple of the OTD guys, will be sporting their Sifferts (or are they now the "Seinfelds"-?), I will be choosing something else in the vintage category!!
Jeff