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My philosophy has been to keep and or acquire the car that would be the hardest to replace down the road. Or another way of putting it is keep the one that will have the highest value over time. In your case I'd probably opt for the 993.
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'73 914 2.0, '74 911 Coupe, '74 911 Targa
'78 924, '84 944, '86 944 Turbo, '84 911 Coupe
'84 944 (current), '96 993 Coupe (current)
'73 911T Coupe (current)
'88 930S M505 (current)
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