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As Adam said, the key is trusting the seller. Positive feedback on the "auction site" of note is key... always read past auctions of the seller's watch items.
If you are willing to shell out $500, go with a near mint Omega from a reputed seller. Buying a cheaper one in mixed condition just opens up a greater possibility for needing servicing.
But I would DEFINITELY pin the seller down on an accuracy test. So many of them say "good" or "excellent" time accuracy. What does that mean? You want numbers. Deviations in seconds per hour and day. Unless you are planning to wear the watch for a day or two and then tuck it away for a few weeks until the next time you wear it, it is preferable to have an accurate watch that could work as a daily wearer. This is an especially good point if you think you might sell it in a year or two.
The other thing is, be patient. Observe the Seamaster auctions of the past and current times. There are many variations in style (dials, hour markers, hands, casings, lugs, etc.), and movement calibre, so find a few that suit you. Once you've established the look you want, create a favorites search that you can run at any time and observe the latest auctions. Also, I'd lean more towards full rotor movement (bumper is older and probably needs more maintenance over time). Some Seamasters have chronometer grade movement, which is a "nice to have", although according to Derek with vintage movements over 30 years old there is virtually no difference in accuracy capability between certified and non-certified movements.
I got lucky with my first Omega Seamaster De Ville. The seller adjusted it and it is keeping exceptional time. Plus, I just love the design... a timeless classic (no pun intended). I nabbed mine for around $300, in excellent condition overall (not mint, but good enough).
Good luck with your hunt!
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