For over a year, my portable audio player of choice has been a 60GB iPod Photo which I have loaded a good chunk of my music collection and podcasts that I have been downloading (manually I might add; I have yet to find a podcast download tool that fits my requirements). Unfortunately, I started running out of space on the iPod about 6 months ago and have been juggling podcasts and albums in order to keep a little bit of free space on it.
During Apple's recent iPod announcements, I had been hoping for an iPod that could hold more than 80GB of storage. Thankfully, a 160GB iPod Classic was announced, and while the iPod Touch was enticing, the limited storage (8GB and 16GB) put it off my list immediately. Sure, the other option would be an Archos 705 player with a large touch screen, WiFi, various video codec support and a 160GB model, but I didn't care much for portable videos and didn't really like the feel of the previous model.
The iPod arrived Tuesday morning while I was at work, so I didn't get my hands on it until that evening. After carefully opening the boxes and removing the plastic wrappers, I was relatively surprised at the slim profile and the feel of the black, metal case. Comparing it to my 60GB iPod Photo, I preferred the smooth transition as I slid my finger from the front to the side of the iPod, while the iPod Classic has a slight ridge.
As far as the bundled headphone, it stayed in the box since I already have two Sennheiser headphones (HD560 and HD580) at home and a Bose Quiet Comfort set at work.
After plugging the iPod into my laptop, registering the device and scanned through the options present in iTunes and on the device, I decided to plug the iPod into my main workstation (which has a Gigabit Ethernet connection to my file server, versus a 100Mbit connection for my laptop) and started to load a good chunk of music and podcasts on to the iPod. Since I do not manage my music library or my Podcasts directly through iTunes (good folder management, file naming and tagging, and crafted playlists work for me and other devices), it was basically drag-and-drop the files/folders/playlists on to the iPod in iTunes.
Just as a side note: even though I do not use iTunes to manage my podcasts, I do import them into iTunes into the appropriate playlists, add or correct any missing or incorrect album art and set the "Skip while shuffling" flag. This works wonderfully on my iPod Photo since I routinely use the "Shuffle Songs" feature of the iPod and do not want podcasts (or spoken word tracks) to get jumbled in with my music.
After loading the initial set of music, podcasts, photos and videos (Podstar Runner FTW), I unmounted the iPod from iTunes and changed a handful of settings on the iPod (such as: setting Shuffle to Song, Repeat to All, enabled/disabled a couple of menu items and reduced the backlight to 40%). I then plugged the iPod into my Hi-Fi and started playing a track from the "Wait Wait... Don't Tell Me!" podcast playlist that I created. That worked fine until the track ended and started playing again. Being a little miffed, I chose another track from the playlist and decided to skip around; upon pressing "Next", it starts playing the same track again. NOT what I was expecting based on the behavior of my iPod Photo.
I also wanted the check on the menu responsiveness of the iPod Classic versus the iPod Photo and found it to be a tad bit more sluggish than the iPod Photo. Also, the touchwheel seems to be a bit too sensitive at times, but not as responsive at other times.
Other than that, I haven't messed around with the new iPod yet and decided to carry my iPod Photo to work until I can find a resolution to the issue noted above.
I'll post more about my experiences with the iPod Classic as I use it more.

Shuffling behavior of iPod Classic
After posting a question on Apple's Discussion forum, I received replies back stating that the shuffling/"Skip while shuffling" behavior has changed with a newer firmware for the iPod Video and it was carried over to the iPod Classic.
I guess I'll have to make do with that and figure a new way of handling podcasts on the new iPod.
IPod 160 GB Shuffling Songs
Hi,
I too have the same problem. When I try to skip a song being played and select a new song, but it plays the same song. Is this a bug in the device software or is there any other setting that needs to be enabled.
Thanks,
Suresh
sureindia@sify.com
Song Skipping
The only bug/feature that I know the iPod Classic in regards to songs not skipping forward is if you have a playlist with tracks that have "Skip When Shuffling" enabled.
The way that worked around that with the podcasts that I manually manage is to create a playlist called "Non-Podcasts" which is a smart playlist which I tell it to include all tracks that do not have a genre of Podcast.
Otherwise, I would browse through the iPod Classic discussion forums at Apple's support website to see if anyone else has experienced your specific problem.