New to vintage omega! Which one should I pick?

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Ummm I think that Speedmaster automatic is much more practical and Japanese like smaller watches due their smaller hand so their reduced collection is much better than moon.
When I was there last month I had a tour round some watch shops, and I saw maybe 2-3x reduced versus pro. Prices on reduced were very good, and (cultural generalisation I know!) the Japanese care for things, so they were superb condition. If you want a reduced it would be a good place to be. As far as I recall Komehyo had a large stock - the one just across the road (to the east) from Isetan, in 3-chome.