Which watches are considered classic vintage watches, but aren't too expensive?

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Within the budget you mentioned, it should be possible to find good exemplars of the 'alternate' Omega Speedmasters from the 70's, like the Mark II, III, 4 and 4.5 as also the Speedy 125.
 
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In throwing vintage Ulysse Nardin into the mix. Great movements and finishing. And you don’t see as many in the wild.