Regarding the topic of the OP:
I currently have and have been comparing over the last week the iPod touch 2G, the Nano 3G and the Nano 4G.
First point: If you are using the supplied Apple earbuds, it's highly unlikely you will notice any difference in the sound of any iPod. Apple's earbuds just aren't in the ballpark for the task of critically evaluating sound. I know a lot of people use them and have no complaints, but they are simply missing what their iPod is actually capable of sounding like.
Second: A general discussion of music, sound quality, etc., is a highly subjective and personal topic mostly pertaining to the listener's own ears, not yours - you will never get a reliable consensus about what sounds best. Too many variables in the works regarding basic musical preferences and tastes, equipment, environment, listening habits, and so on.
Third: For my own evaluation, I chose songs that were originally recorded in the late seventies to present, generally as diverse a mixture of rock, pop, jazz and dance tracks as I have in my song library. I wanted to see how each iPod would treat music originally recorded in the analog era, the early digital era, and present day across various styles of music. Needless to say, EQ settings were off at all times on all iPods. When comparing identical tracks on each iPod, I would try to match (as closely as I could by ear) the output level of the vocal (if present) as the default standard for matching overall output volume level amongst all iPods. Using that method, I listened to the songs at low, "normal" and high volume.
Fourth: All listening was done with headphones - Bose on ear headphones are my ear bangers of choice (more on this later in response to the Bose comments in this thread).
Here are the results so far:
iPod Touch 2G - The most pleasant sounding, most balanced of the three across the frequency spectrum. Sounds very good in a variety of listening environments, both indoors and out, with a variety of different songs and musical styles. Doesn't skimp on the lows (to the extent they are present on the source recording), good midrange response (so it's not just highs and lows where the overall mids are left for your equipment to figure out), and great sounding, crisp highs that don't become too shrill or overpowering when the volume is cranked. It's the hands-down leader of this pack
iPod Nano 3G and 4G - The Nano 3G has a warmer sound compared with the Nano 4G and the bass frequencies are a little more pronounced. Not that the Nano 4G can't do bass, it can go as low as all three iPods, but the lower mids and/or upper bass frequencies sound like they weren't invited to the party at times. Thus, the Nano 3G sounds a little more punchier than the 4G, especially at lower volume levels indoors and at normal to louder volume levels outdoors. The Nano 4G brings crisp sounding highs to the table, however, so vocals (generally) and instruments that normally register themselves in the higher ranges have a little more definition on the 4G, but not quite the overall fullness and warmth that the 3G has. Generally, the Nano 4G has more of a shriller sound at higher volume levels with it's emphasis on highs and cranking the volume generally doesn't necessarily help the 4G compensate for the 3G's somewhat fuller low end response.
Which Nano (3G or 4G) sounds better? Well, it really depends on the music your listening to. In my opinion, the 3G generally sounds better with tracks that benefit from dishing out good overall low end response (generally, but not limited to: rock, some pop, and dance tracks) and also gives the perception of better dynamic range largely due once again to better low end, lower mid presence and response. The 4G can sound a little overpowering with electric guitars, cymbals, etc., on some rock tracks when listening at higher volume, but it's sounds better than the 3G on some ballads with it's crisper and more defined treatment of vocals, lush strings sections, and generally subdued rhythm section arrangements which generally benefit from the more articulated highs of the 4G. But it mostly comes down to individual songs (at least in my library). Some sound better on the 4G, but most generally sound better on the warmer sounding 3G. Once again, it's very subjective. For example, some folks would rather have less low end response than more and that may at times, abiet silently, color their opinion about how good or great something sounds in a general discussion. In other words, your music library, taste, ear and listening environment may be produce a different result.
FWIW, I noticed a few other things about the Nano 4G: the battery life for just listening to music is generally horrid compared to the Nano 3G and the Touch; the gee-whiz factor of the Nano 4G's accelerometer wears off pretty quickly and it gets to be a pain to flip the thing over for cover flow, videos, and games - especially when you have to mentally compensate for changed click wheel controls. The iPod touch controls are oriented with the accelerometer changes, so it's much more natural to use, and the Nano 3G's landscape screen orientation makes the 4G's accelerometer bag-o-tricks mostly unnecessary and click wheel control buttons are always just as you see them. The 4G, for reasons I haven't been able to figure out yet, seems to sometimes "forget" which is the right channel and which is the left channel, reversing the two. Comparing the track on the two other iPods and iTunes, the 4G was the culprit. Lastly, the Nano 4G interface is far more pleasant to operate, and it's transitions from one screen to another are much smoother than the 3G's comparatively jittery-looking screen transitions. It's just feels like Apple never got the Nano 3G interface performance quite right, so they just gave up.
Regarding Bose:
I'm not a fan of their speaker systems, and I've ever tried their in ear tri-port buds, but the Bose on-ear headphones, as general purpose consumer-targeted phones, sound fantastic to my ears, and the reviews on Apple's store show that, not only am I not alone in that opinion, those phones are one of, if not the highest rated phones on Apple's store. And Amazon's customer reviews are pretty much consistent with the reviews on the Apple store. For the price, the on ear phones are a great deal, and I've used Senhiesers, Sony MDR studio phones, V-Moda, etc.
Just to make something clear: Bose on ear phones are not intended to be, nor are they designed to be, studio monitors and/or phones that faithfully reproduce a professional, pristine, uncolored, flat frequency response curve. These phones are designed to produce music in a way most people will find sounds great out of the box. In other words, it's meant to be plug and play for portable audio devices (aka, iPods) as if the consumer where at home, sitting in their living room couch, right at the designated sweet spot for their speaker set-up, with the amplifier eq'd just right for the music their listening to. And most people's home stereo listening environment/set-up is a far cry from a professional recording studio sound booth or audio laboratory set up for precise frequency response measurement. As the instructions for these phones empathize, you should refrain from using the iPod's built-in EQ options and make sure it's set to off because using the EQ will destroy the sound these phones were designed to produce. I don't know what Bose did exactly to determine what sound properties generally appeal to most consumers, but the praise these phones have received from users seems to indicate that Bose got it right this time.