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6 digit all the way for me. The bracelets and clasps on 6 digit are miles better than than 5 digit. That being said I still love the brighter color of aluminium bezel on 5 digit GMT which is why I currently own 2 of the 6 digit Rolex and one 16710 Pepsi.
I think it is a trade off here, do you have any particular thing that you really like on the older model to for go the much more superior build quality of the modern day Rolex? There are reasons why some of the older/vintage/transitional models price are significant higher than the current model which are still under production.
I would say go with the one that really "speak" to you. No matter its 5 or 6 digit, any Rolex should last a life time :)
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