Well, I finally decided to go through the last couple editions of Wristwatch Annual to take a look at which watches I might recommend for Jeff's friend. I had been afraid to do so as I really didn't want to tempt myself at the same time! But, after a few glasses of Chardonnay this evening, I went ahead and pulled out the references and I have come up with a few watches that catch my eye and that I'd be happy to wear. None of my choices are vintage watches simply because I knew others would cover that topic better than could I. I tried to look beyond the popular and obvious choices since it's always cool to put something on your wrist few others own, or have ever even seen before.

1) Eterna Kon Tiki Chronograph (42mm) or Eterna Kon Tiki Four Hands XXL (44mm). Both come in well under the $5K budget (for one watch). These are shown in the Wristwatch Annual 2009 and 2010 editions. I just love the large green triangle indices at 3, 6, 9 and 12 o'clock. Here's the chronograph version:

2) Here I differ from Mark Moss whose knowledge and interesting comments I always enjoy, and, learn something from. I just love the Breitling Navitimer! I like both the "conventional" Navitimer A23322 and the Navitimer World and recommend either. I tend to choose a watch for its eye appeal (solely to me, that is) as well as its legibility in any light (or lack thereof). Below is my Navitimer Montbrillant Edition A48330 which I bought 4 years ago because I love the gold indices set against a stainless steel case and black dial, its brown croco strap and the fact it is a manual wind version of the Navitimer. The 18kt gold cased version was a limited edition while this stainless steel version was not intended to be. Apparently it was not a "hot" seller so it was only in the line 2 years and never appeared in any Chronologs. I find it very easy to tell the time with this watch and it is my most frequently worn watch. Jeff's friend could probably still find one at a Breitling dealer with a bit of hunting around.

3) RGM Professional Automatic Diver - 43.2mm with 2892 movement. This is an American company located in PA, very close to Lancaster where the venerable Hamilton brand was manufactured before they were bought by the Swatch Group. This watch is slightly reminiscent of the Blancpain Fifty Fathoms. I'm sure most of you have seen pics of it before. Very well made, highly legible and a cool look, too. Here's a (little) pic from their website (hope that's okay):

4) Seamaster Aqua Terra Co-Axial or, Railmaster - Very simply, classy dial with great visibility, especially the Railmaster with plenty of Superluminova. I like the 42mm version and own a Railmaster myself. Both watches, in my opinion, look much, much better with a brown croco/alligator strap versus the stainless stell bracelet. The stainless bracelet makes these watches look too plain for my taste. Very narrow bezel so the dial is big and very easy to see with just a quick glance.

5) Bremont Supermarine 9500/BK-GN - This 43mm watch, with its cool green accents on the bezel and dial really captures my eye. I think it is a stunning watch and once again, great visibility. Yeah, I wear contact lens and am now at the age where I need reading glasses, too. Bummer! Here's a pic I pulled off a google search (hope that's okay):

Since several of the above watch recommendations are below the $5,000 budget, perhaps Jeff's friend could add a second watch. He could use it as a "beater" as this might push him into our league as collectors once he gets used to switching from one watch to the other. That's what did it for me, LOL!
My "extra" choice would be the new, soon to be released Hamilton Chrono-Matic Pan Europ as recently seen on this page as well as Hodinkee. I like it quite a bit.

Well, this was fun and I didn't have to spend any money, just Jeff's friend's money. I hope he likes some of the choices we've all recommended!
Steve