Wow, what a lot of posts and not even one mention of a Zenith. The new ones are a hair beyond 5K, but a vintage Primero....or rather THE vintage Primero, ref A 386, should be within striking range

I'm ambivalent about the Speedmaster, if only because everyone has got one. In its place, I would propose a vintage Seamaster with the same engine in its place - maybe the soccer dial - or a cal. 1040.
The 73633 is a great pic, as is the modern Carrera
After that I get lost in vintage Zeniths again, but that's just me...

: Just for fun, and to help a freind make a selection, please list
: your top five chronograph recommnedations for a new collector,
: with a $5,000 budget. My friend seems to like the stainless
: steel classics, with round cases -- Speedmaster, Carrera,
: Navitimer (he likes shape of Navitimer, but not all the scales,
: etc.), IWC Portuguese, etc.

: Assume that he is indifferent, as between vintage and modern, but
: let's be sure to give him some good modern (new) choices. Some
: folks are happier walking into a store and making a purchase,
: rather than dealing with the whole vintage thing.

: Jeff