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Aren't the ones that are currently the most expensive more likely to go up most because they're the rarest?
Dramatic_Hammer-
Different models from different generations appreciate/depreciate differently, so while a current gen GT3 might be holding value, some model 996s are appreciating at an eye-opening rate.
In this particular circumstance, the market seems to be quite interested in pre-facelift 996s. On the face of it, it appears to not be driven by anything other than internet conjecture which is frankly, worrying if you're "small-time" investing, but if you're on the button on that internet conjecture then you can do OK.
@Hefty says it's because the pre-facelift has a healthier 3.4 without IMS issues, but when you look at the stats of how many 3.6s actually had an IMS issue, it becomes more apparent that it's more of an internet problem than a real problem, hence why saying it's driven by internet conjecture.
NurseHolliday
I'm assuming it's because buying and selling progressively more expensive Porsches has a bigger ROI than pure saving.
It's about predicting which ones are going to go up in value the most, because otherwise as your current 911 increases, then the one you want increases too, thus negating the profit you've made.