[Perfectlap]

The best option for an out of warranty Porsche is low mileage. Not too low like the car just sat around for 10 years only coming out of the garage for a monthly drive. Don't tip the scales in favor of one car over another because of options, #1 priority should be mileage, it's more important than even year.
Case in point, first 65-70K miles of ownership of my car: $500 in repairs, TOTAL.
Mileage after 70K miles up to the present 97K: $15K in repairs. And only about 1/4 to 1/3 of that was labor,it was mostly the expensive parts.
The only real exception to this are cars that live out their lives in moderate weather like Southern California. If the car sees extremes of heat or cold and less than stellar roads, moderate to high mileage repairs are going to be $$$$$.

And let me give you this advice too about year while we're at it.
1997-99 is basically the same car.
2000-2004 is basically the same car.
2005-2008 is basically the same car.
2009-2011 is basically the same car.
2012-2014 is basically the same car.

Once you've decided between S model or base, look for a specimen with the lowest mileage in each of those productions. Extra points for HID (a.k.a. Litronics , a $2K option), 18" factory wheels ($2K option not including tires), hardtop ($1400-1,800), a new canvas top with glass ($1500 upgrade) and GT3 aero bits ($1K bumper, maybe $800 for side skirting). The most important upgrade? A new IMS bearing: $3K including clutch (2000-2004 cars) and water pump (all cars) $1k at shop rates including labor. Water pump should be replaced every 4-5 years regardless of mileage to prevent head cracking or disintegration of the plastic water pump blades into the engine, both MAJOR EXPENSES avoided by simply spending $1k, much less if its DIY. That IMS bearing should be replaced as a first order of business on any 2000-2004 car that you are a) unsure about either oil change frequency or b) the driving habits: frequent drives good, the longer the better... Infrequent driving consisting of short trips (less than 30 minutes driving) not good. And I would NOT wait for the clutch to wear out. That's not a gamble worth being wrong about just to defer a $3k expense you'll be doing one way or another. Get it done, enjoy the car.
And definitely get a PPI inspection that includes a compression and leak down test -- If the cooling system was not looked after, you don't want that car.