Well the original post is pretty old but I can speak directly to the S2000 vs. Sky Redline comparison as I have both sitting in my drive way. I was originally considering buying the S2000 or the Sky Redline myself and opted for the s2000 CR (granted I am a honda fan having driven a Prelude SH for the last few years). My girlfriend then purchased the Sky Redline and had the GMPP turbo upgrade put on it. If you are going to buy a Redline the GMPP should be done to it. For less than a thousand dollars you get around 300hp to the wheels and even more torque. Unfortunately the dynos charts for the sky were lost so I can no longer give the exact numbers.
Which you choose is very dependent on what you want out of the car. A lot of people don't understand the s2000. Anyone who says things like the s2000 needs a v6/v8, heat seaters, or a better audio system misunderstand the vehicle. If you fall into this category you should probably buy the sky. I'll break the comparison down into sections so you can decide which one is best for you. I already know the s2000 is the right one for me as I chose to purchase it. The Sky is a very good car (albeit not one I would choose to own). The general break down though is the s2000 is better when you need to steer and the sky is better when you want to just mash the gas.
Price/Performance Ratio:
The Sky wins this one, it is cheaper and has better horsepower/torque numbers. Both cars are quick vehicles. The power to weight ratios are actually very similar in their stock trims, however with the GMPP upgrade the Sky has a formidable advantage here, and it will still cost you less than an s2000.
Luxury/Build Quality:
This is pretty much a tie. Neither car competes as a luxury vehicle. The s2000 has a much higher build quality then the Sky, this can be seen in both the interior materials heard in the rattles. With the top off of my s2000 CR and the top down on the Sky the s2000 is much quieter when on the highway or even driving at city speeds. Conversely with the top on the s2000 CR and the top up on the Sky the Sky is much quieter on the highway and about the same at city speeds. However it should be noted the s2000 CR has all its sound deadening material removed and has more track oriented tires on it, so I imagine the base s2000 is much more comparable. The s2000 has much less wind buffeting than the Sky, even if you purchase the after market rear wind diffuser.
The s2000's seats feel very nice and hold you in position, the sky's seats have the tendency to bounce and squeak a bit. The base s2000 comes with a powered soft top that is supposedly very nice. The sky's soft top is very cumbersome to close due to the clam shell design of the trunk. Also my girlfriend's trunk leaks and the water builds up in her trunk, she has yet to be able to remedy this, however I haven't heard too many other people complaining. The sky's trunk is also very easy to close incorrectly. There is also an issue with the top's rear hold downs breaking, which has happened a few times to the sky, although has been replaced by the dealerships for free.
The s2000 has terrible cup holds and yet the sky manages to be worse (some models have cup holds between the seats which are much better than the passanger's foot well cup holder which always pops out and breaks, 5 times last I counted). However the Sky has On-Star which has GPS service built in if you pay the subscription fee. The On-Star service is actually pretty nice as you can even have them find hotels and restaurants for you. It can come with a 6 disc changer and has an audio input on the radio. I mention this because the s2000's radio door and gear shifter makes it slightly more difficult to replace your radio with any units that would provide. The sky also provides more general climate and audio features, however the s2000's systems are extremely easy to navigate while driving. Interestingly the driver-centric design makes the passenger's view of the car seem very boring.
A bonus for the s2000 is that it has strong AC fans so you can be more effective when the top is off. It also has what I call "convertible vents", which blow air only on your legs. This is great when youve got the top off at a stop light and the sun is beaming down on you, as otherwise your legs will get very hot.
Racing Performance:
The s2000 wins this category easily. The Sky is more prone to over-steer, while the s2000 is far more neutral. The s2000 is also has far faster response to the steering wheel than the sky does. If you purchase a sky the second thing you do after the GMPP upgrade is put new tires on it as the stock ones are crumby for the car (a cause of the poor handling and the ABS system being jarring). The Potenza RE-11 tires have vastly improved handling and response in the sky. Both I and my girlfriend drive the cars in auto-cross and the s2000 turns in much better times than the sky, even after the sky had the GMPP and RE-11s put on it, both when I drove it and when my girl does.
The s2000 can and will spin out very easily, Ive done it several times in Auto-X and a lot of people have wrecked s2000s for this reason (they refer to it as snap-oversteer). The Sky is much more forgiving in this regard, but it is a direct result of the fact that it is tuned for under steer. I have the feeling with an alignment change either you could make either car fairly neutral as their weight balances are almost perfect.
For the track the s2000s traction controls are easier to disable as well, as some traction control always seems to be on with the Sky. As a side note for bragging, I took the s2000 to race at Summit Point and I was able to lap everyone else in the beginner group my first time there, and I wasnt allowed to pass in turns which really slowed me down. (This is probably largely to do with my auto-x experience, but the car is extremely capable in this environment).
Street Performance:
Either of these cars is better than what the average person is driving around. I mostly consider this a tie, maybe slightly favoring the s2000. The big thing is, if youre a red light racer youll want the sky; after the turbo tweak it just accelerates much harder than a stock s2000 can. Heres the thing though, a lot of people look at the s2000s low peak torque and the skys high peak torque and automatically assume the sky is easier. In a regard theyre correct, if you want to accelerate in its much easier to just punch it in the sky without changing gears than the s2000. However in city driving the sky is extremely easy to stall when starting off. The reason for this is the torque in the Sky before the turbo kicks in is extremely low, lower than the s2000s. Part of the reason for this is the low-compression the engine is running at due to the turbo running at such high psi. This also causes the s2000 to lug around better than the sky does when youre in stop and go traffic. Both cars offer bumpy rides, but the s2000 always seems more planted and the sky seems to bounce around a lot due to the seats. As a note if you grew up driving naturally aspirated cars with 2.2 liters of displacement or less than having to rev the s2000 wont seem like a big deal to you.
Ergonomics:
The s2000 is a big winner here. Here is a list of things on the sky that suck. The window controls for the sky require you to nearly break your wrist due to the very rearward placement. The seats basically require you to open the door to adjust how far theyre leaning back. Those nice looking fenders dramatically reduce visibility.
The s2000s layout is almost exclusively centered around the driver, your AC, lights, and radio are all controlled right beside your steering wheel. In fact the rest of the dash looks very empty from the passenger seat because of the lack of controls visible from their perspective. One thing that I hate on the s2000 is actually their racecar inspired start button. It pointlessly adds another step to starting the car and is one of the only features the car has that dont either make it go faster or help it be DOT legal. If they had added features like newer cars that have RFID chips so you dont have to insert a key to start the car than itd be no big deal, however they never added that option. The s2000s shifter is one of the smoothest available as where the skys transmissions is pulled out of a truck and you can tell. It should also be noted if you want to spruce up the interior of the Sky you cant replace the shifter knob as it isnt a standard screw on design for some reason (or at least my mechanic couldnt even get it off without fear of breaking something). The s2000s trunks infinitely more useable than the Skys, and the hidden compartment in the s2000 is probably about equivalent to the skys glove box
although if youre looking for storage space the neither car is the one you should get. For these reasons I consider the s2000 slightly more practical than the sky, but again, this is the wrong motivation for either car. Both cars also have very poor rear visibility with their tops up, and excellent all around visibility with their tops down (The CRs visibility marginally worse due to the huge ugly functional wing on the back).
Summary:
If youre looking for a car that most resembles a race car the s2000 is your pick. If you cant live without turn by turn directions the sky is your pick (there are very few places to mount a GPS in an s2000). If you want an automatic transmission you have to buy the sky (and I dont think you should have a sports car unless youre missing your left foot). If you want to blast past people at lights youll want the sky (on the highway either car is equally as good, the s2000 better if you want to do it during a turn). If you mostly want a car to relax and look good in simply pick the car that you think looks the best.
Also I just want to say this is the only comparison thread that didnt degenerate into a Jap Crap vs. American Crap argument. I hope this was useful to anyone comparing the two.