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2nd Gen 16GB is the same exact as 3rd Gen 8GB just less storage. If you got 32GB 3rd Gen you will be eligible for OS 4.0

You can still get the 4.0 update with the 2nd gen iPod, you just can't multitask, which isn't even a big deal because you can just jailbreak the touch if its that big of a deal for you.
 
I'd go with the 3rd Gen, 8Gb, it's the newest thing out there and it has more than enough space for me.
 
I'd go with the 3rd Gen, 8Gb, it's the newest thing out there and it has more than enough space for me.

Doesn't really add anything new though, so you might as well go with the 2nd gen with more memory. You think that 8 GB will be enough but in reality you are not getting 8GB of space, you are getting like 6 GB. about 2 GB is reserved for the OS and drivers for the touchscreen and such. If your going to spend the money might as well full proof yourself for a couple years, 6GB's is nothing for an iPod. Unless you are just buying it for the internet, get something with more space. Here is an example.

I have the 16GB iPhone 3G S, which is actually 14.3 GB.

Songs - 116 (819.6MB)
Video's - 4 (3 movies, 1 TV show) (5.03GB)
Photos/Video's -74 photos, 12 videos (366.8MB)
Apps - 99 But 21 come pre-loaded with my 3G S, so I've downloaded 78 additional Apps. (3.09 GB)
Other - Text msg's and phone data I'm guessing? (332.1MB)
Free Space - 4.68GB

Total space used 9.62 GB's
 
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