If you like Chronographs an early 861 Speedmaster in great condition is nice, if you like divers its a bit harder as a lot of them that are vintage aren't really worth risking in water anymore, if you like dress watches a nice Constellation Deluxe looks superb with a suit. In the Omega world the 60s era Seamaster 300s are about the best fit in that price range, don't get a watchco or a "NOS" one, just a nice clean honest example.
Doesn't have to be vintage but my last few purchases have been new watches. Would like a more casual one
I have a lovely 1978 Baby PloProf that can be yours for just £2500 You could get a nice no date vintage sub within your budget... actually you could get a lot of things within your budget. Might be worth narrowing it down a bit, or some wag will suggest a Swatch Sistem 51, and that you send them the remainder of the budget
that 5k region is filled with a large range of quite high quality watches. I imagine something like a well used GMT Master would start to show up at this level. even a good/excellent DJ or DD would comfortably drop into this price point. what are you looking for?
321 Seamasters? Check. 861 of most Speedies? Check. 60s SM300s? Check. Datejusts? Check. Military Chronos? Check. El Primeros? Check. Camaro/Autavia/Carrera? Check. Lots of options...would even hazard a nice JLC Memovox in there, or a slightly used PP/VC...
Omega seamaster banana. Nice pop of colour. They don't seem to come up for sale all that often and many seem to come with service dials.It will come in well under budget too.Here is mine
How about a military issued diver... obviously not Omega or Rolex, but you could pick up something supercool like a RAN Certina DS-3 Super PH1000M, an early eighties CWC auto, or maybe a Benrus Type 1. I also love the IWC Ocean 2000, and you could get a nice civilian one for that price.
80's - 90's Rolex Submariner could be nice if you don't already have one? Based on my recent research GMT masters will be a little above the budget. In fact I've spotted a number of the new ceramic no date submariners going for right around $5700 for compete sets...classic iteration of the quintessential dive watch! Also allowing you to avoid the quagmire that is vintage Rolex
I have a 1990 Explorer II polar with killer patina...not really vintage, but a great look. Will be coming on the mkt soon.
I think most folks have said it all and it's a nice problem to have. Personally I'd go vintage route and look on here, some gorgeous stuff for sale and you can buy with confidence. The bay can be a minefield but there are still 'bargains' if you're feeling lucky. Good luck anyhow and let us know what you get my friend.