Paul S replied: "These are two very different cars, each with some good points and bad points. As a general rule, it's often said to get the newest 911 you can afford... though in this case, the differences in the cars may be just as much of a defining factor as to what you want. I regularly drive an 80s 3.2L 911, and have spent alot of time at the track in friends' and students' 996s and a few 997s: 911SC and 3.2L Carrera: Great cars. Very reliable, and with a great amount of after market support. Either of these models can be expected to run for a long time before needing engine rebuilds, but these are 20+ year old cars now, and many will be showing their age. Ergonomics will feel very dated as the basic design was about 20 years old when these cars were produced! And while parts can look attractively priced when compared to newer Porsches, overall, you will still find they are reflective of the fact that these were very high end cars when they left the factory. They are very fun cars to drive, and a challenge to go fast in (but still very capable). Most likely trouble spots would be the exploding airbox and clutch in the 911SC (probably rare that you will find any of these cars that haven't had these addressed by this time), and valve guide wear in the 3.2L (more common in the G50 equipped cars of '87-89, but has been seen in all, as well as with the SC and later 3.6L models). The 3.2L Carrera's DME engine management is a nice upgrade compared to the 911SC's CIS, but an excellent condition SC would be better than a lesser condition 3.2L. 996: The '99 and early 2K models are good cars that are now available at some very attractive prices... sometimes prices that place them quite close to their older aircooled version just mentioned. There is no dount these cars are much faster (having turned a few laps driving a friend's 996, I jumped out and into my car before the end of the session, and my first impression was "I am all the way on the gas, why aren't I going anywhere?"). But... many see them as lacking the charm and character of the older cars. On the plus side, they are easier to drive, have modern features, and great performance. While they are high end cars, my experience suggests their build quality is not on par with the 993 and earlier models which had much more hand assembly and greater engineering tolerances (though still well above many other cars in these areas). If you really want an older, "classic" 911, you may find the newer car lacking in many of the characteristics you really want. Conversely, if you want a faster, more modern car, the older car could leave you very disappointed. If it is the classic car you want, then a pre-purchase inspection by a knowledgable Porsche mechanic is a must (probably good for any car, but moreso with a 20 year old car)... the money you spend here is to find out if an engine rebuild is in the near future or to find any other signs of problems. In either case, be willing to pay a premium for an excellent condition car... in the long run, cheap Porsches are far more expensive!"