hashluck
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I don't know Porsche inside out and I am not a mega fan, but I do agree 996s look to have just started coming out of the bottom. They can be a scary/expensive purchase though if you don't know what you are doing or are looking for, probably as they got cheap enough to fall into the wrong hands.As a Porsche enthusiast, I'd go for a clean sub-50k miles Porsche 996 Turbo.
The GT3 is way beyond the budget as is anything Porsche with tge coveted RS badge.
I know the marque inside out. So I'd not step outside and risk buying a bad example that could be a money-pit. I can spot a money-pit Porsche from a thousand yards and a look at the service book.
Perhaps not as an investment but models you should not lose too much on and hopefully have at least a neutral experience with allowing for running costs would be the 987 Gen 2 Boxster and Cayman. None of the issues (perceived or otherwise) of the 986 and 987.1 as Porsche designed them out and made lots of little changes that added up to a lot. They are surprisingly rare as they did not make them for long and that was during a recession. Very contemporary to look at still, great to drive (and flattering) and can be a daily or a nice day car. Easy to own and you will not lose much (if anything). I agree with those who say go for the Cayman R if you can stretch to one as the best 'investment' choice.