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I'm no expert but plenty of experts here. Honestly I would go straight to Jacek at Tropical Watch and strike up a discussion.
I think 5 digits are the sweet spot between new and old with the older design but mostly modern movements. But some people like the aged dials, patinaed lume and so on. Just have to pick something you like.
Also with the 5 digits there is enough supply not to make fakes and frankenwatches/artificial aging as much as a worry. But it happens. It's a tricky market and gets trickier the older you go.
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