So generally speaking I think the best value in these are 3rd generation ceramic Seamaster Pro 300M divers by far, they can be found around $3,000 which is IMO quite worth it. You can pay about $800-1200 more for a 4th generation but it isn’t a straight upgrade as its a larger watch and the thickness of it makes it somewhat less comfortable on the wrist, Cal 2500D and the ceramic bezel are excellent, durable and easy to maintain so that’s the sweet spot in gen 3.
Rough 1st and 2nd generation Seamaster Pros are cheap, often under $2k, because the cost of maintenance is high, that cost is mainly related to the bezel, which scratches easily and can only be replaced with a whole new assembly if using genuine parts. This is a big expense on top of the cost of a movement service, and as a result examples with good bezels or freshly replaced bezels carry a high cost accordingly. There are also a lot of less scrupulous dealers who fit aftermarket bezels to these to save money, and that is only increasing.
The second generation is the least desirable imo as if has earlier Cal 2500 variants (pre-D) and the fragile painted bezel.
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