Having had an NSX for 7 years and now owning a 1995 F355 Berlinetta, I think that they are both great cars, just different. Peformance wise they are not that far apart, looks are going to be purely subjective, but many consider the F355 to be a classic design and the last pretty Ferrari. Soundwise, I spent a lot of $$ trying to make the NSX sound like a Ferrari, it is not going to ever work, it sounded great, but it did not sound like a Ferrari. The NSX only cost me about $7,000 in repairs over 7 years, mainly a/c issues, window regulator and clutch as well as scheduled service. I have spent close to that getting the F355 correct and up to date on maintenance. Once the F355 is properly sorted, they are fairly reasonable with the exception of the major service every 5 years at $7K at an independent or $13K at a dealer. The only F355s that are trading below the mid $60K range are dogs and storied cars that I would run far away from and they are without proper paperwork and service records. If you are looking to buy one, buy the best you can afford, the $$ spent on getting it correct can eat you alive. Just like wanting to avoid an NSX that is in snap-ring range, you want to make sure the the F355 has had the valve guides replaced ($14K) and that it does not have header ($6K) or cat ($3K) issues. If the maintenance costs scare you, stay away from any Ferrari, they are not that troublesome if you perform the proper maintenance with a qualified mechanic (the dealer is not always qualified, in fact they may the worst palce depending on where you are located). You will be able to rack up the milage on an NSX and not effect it re-sale price too dramatically, not true with the Ferrari (over 30,000 miles will be difficult to sell). The other thing to look into is how the local clubs compare. The NSX club in Denver was very informal and really only had 1 event a year, I put it down to we all are too busy working to schedule events. The local Ferrari club has 3 incredible events in the last 3 months (they have more time and $ to plan would be my guess). My last advice is really drive the F355 spider for more a day, rent one if you can and determine if it worth the cost difference to you, and only you, it is your life, your money and your time, you only live once so get the one that puts the biggest smile on your face.