Such decisions rarely are made on a purely rational basis. If you aren't taking the car to the track, ANY one of these cars provides performance FAR beyond the humdrum of daily transportation and would be fully capable of earning you frequent speeding tickets. It all comes down to how much you like the styling, how much you are itching to make a change, and how much cash you have burning a hole in your pocket.
If you have a lot of money burning a hole in your pocket, and if you really like the new styling, get the 981. It's definitely cool to own the latest thing with a full warranty. It's a little uncool because you know darned well the dealer is going to gouge you for every cent they can. Who cares if you have the cash. You can always make more. So, do you have the cash sitting around to make it happen?
If you are just itching for a different car with a warranty, or if you like the older styling better, maybe the 987 would be a nice compromise. Getting a 2009 or 2010 might get you a vehicle with a warranty and no IMS to go bad, and ought to cost a lot less because the first owner took most of the hit on depreciation, and the depreciation will only get worse with a brand-new model out there on the streets.
Also I think it kind of matters who you hang out with. If they are all Porsche guys, then you'd want the latest thing in the "S" model to have some respect. If all your friends and family drive Hyundais and Buicks, then ANY of these cars will always be a "Porsch" and they will think you spent $100K whether you actually did or not.
Financially your best bet would be to keep your 986; however, if you are concerned at all about finances, spending a bunch of money for "upgrades" to your 986 would be throwing your money away. You would be better off financially to just do all proper maintenance and use your existing 986 as much as possible. The $10K in "upgrades" could be kept in the bank for a down payment on a new car in a couple of years.
But again, these decisions aren't made on rationality, it's whether you have the uncontrollable itch and the cash to make it happen.
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