I thought about buying a S2000 before I got my N. I was driving a TTZ at the time and thought about using it as a trade-in for a newer sports coupe. I test drove one and as soon I got into it I thought I was going to die if anything hit me. The damn interior was so tight and small (the door sill is so damn annoying). I am by no means a large person (only about 5'10ish) and it was not comfortable to for 20 minutes so i doubt I could commute in it for 5 hours. The 300ZX and NSX's interior is lot more roomy and comfortable, with the 300zx's interior being a bit roomier. Getting out of these cars are also a lot easier.
The S2K is a smaller car, but yet it's taller than both 1990s coupe. I must say though, that the driving position is much better in the 90s coupes, by far. As soon as I sat in the NSX and drove off to test drive it, I knew that it was coming home with me. I have never experienced such a great driving situation like the NSX or Z32 (The NSX is so similiar in layout and position that it was like I didn't even need to adjust to a new car) and I have commuted for 5 hours straight many of times in both of them. I joke to all my friends sometimes that the car was designed for me.
As far as power goes, needless to say the S2k test drive was disappointing. The power takes forever to build in first gear and I just really do not understand how anyone gets the thrill out of driving a S2k on the streets. You have to rev the hell out of that thing to feel any kind of power sensation and that's just madness to drive like that daily. In no way am I saying that the S2000 is slouch, but you have to drive like a madman to experience some daily torque doses. With the NSX, it's not an issue, power is always on tap and then you experience the same effect as the S2k at higher RPMs, except it sounds, feel and looks even better.
I respect the idea and efficiencies of the S2k, but I honestly believe the NSX is a lot more pratical. Larger cargo/trunk space, better interior space, more power, more exclusive, better looking, dare I say safer and also a removeble roof if you get a NSX-T. I say SELL the S2k and get an NSX. Each year has their advantages and disadvantages as many different owners can argue, but at the end of the day, you still own a better car compared to the S2k. You'll never look back, there is no dilemma.
If you can afford it, GO FOR IT. That's the only dilemma. Try to find a lower mileage one as there are plenty as in percentage wise. I feel that buying a higher mileage NSX for a few grand less than their value is pointless if you have to spend some extra money on fixing anything that is worn and then you will have spent the same money on car with more use/mileage. Most owners who buy these cars have surplus income and will take care of them. Mine had like 15k miles and the guy had the courtesy to do the 60k service before he sold it.
Just my 2 cents.