Here is my list, order of the watches is not important.
1. Omega Speedmaster professional ( aka the Moonwatch ): If possible you take a pre-moon reference 145.012.
2. Rolex submariner 5513: It's a better choice than any Submariner 1680 ( yes even the Red Sub ), no ugly cyclops that ruins your great dial, still affordable although getting more expensive very very fast. If your budget allows it you go for the Submariner 5513 gilt dial. Rolex Submariner 5513 gilt
3. Heuer Autavia 1163 MH with ridged markers: It's the best Heuer watch to buy at this moment. It's Derek Bells' watch, it looks great, it is still affordable and has a crazy potential. You buy one and in 5 years the value will have doubled or tripled. If you can find an Autavia 1163 Chronomatic ( Viceroy colors ) you take that one and just forget about the other 4 watches. Why not the 1163 Siffert many will ask? I had the Mark4 and Mark6 and believe me the Derek Bell is your watch!
4. Jaeger- LeCoultre tribute to Deep Sea: This is a re-edition watch that is amazingly close to the original diver. If you can find the original you go for that one and forget about the other 4 watches. Of all the non-vintage watches this trubute JLC is the best watch money can buy. Jaeger-LeCoultre tribute to Deep Sea
5. Universal Genève "Nina Rindt" Compax Chronograph: This one will be a little harder to find but certainly not impossible. It's a no-breainer. If you find one for sale with subregisters going tropical, just take it. Universal Genève "Nina Rindt"
So, is this the best "5 watches" list? I really believe it is. I took my time time for it and I can't imagine a better list. Of course some of you will argue that the Zenith El Primero A386 has it's place in it. That might be true from a historical point of view but I just don't like the look of that watch. And what about the Blancpain Fifty Phanthoms? Great watch but better than my 5 picks? Think not. If you think you have a better list ( I am sure you haven't ), please shoot me a mail.