Pros: Highly modifiable, good battery life, storage space
Cons: medoicre sound quality stock, iTunes, price point slightly high, iTunes interface?
I purchased the 5.5gen black 80GB a few years back in the late spring of 2007. This has been one of the best electronic investments to date. My purchase was based on two key, determining factors.
1.) Storage Capacity: This thing had 80GB of storage, this was the biggest capacity of any portable music player available at the time, and still remains high on the list
2.) Modifications: This thing has it all. Since the iPod gained so much popularity it's easy to see how prevalent docking stations, line out devices and other peripherals there are for the iPod, but that's just half the goodies.
a.) Storage capacity: If this is you biggest concern this iPod is for YOU! I need a large amount of storage because 90% of all my music is lossless. If 80GB isn't enough - check this out. A company by the name of Apricorn Inc. makes a hard drive upgrade kit for both the 30GB, and 80GB 5th gen versions, boosting capacity to 120GB and 240GB respectively! (see website for more information)
This is amazing storage capacity for a portable player. I was constantly having delete and replace files on my iPod because it was operating at max capacity, yet it only held a fraction of my music library.
b.) Audio upgrades: Red Wine Audio makes the iMod for 5th gen iPods. I have not purchase this mod, but have listened to an iPod that was iModded. There was a drastic difference in sonic clarity. IMHO the 5g sounds better than the classic iPod anyways (after 5.5g the Wolfson audio codec chipset changed to a Cirrus Logic one). Now there are many other portable music players out there that sound better than the stock iPod, but can't reach the sonic fidelity of the iMod without serious research, and risk.
c.) Operating System: AS-IS the factory iPod interface really isn't that bad. However,there are those who hate iTunes, or the iPod interface. Three features (or lack there-of) desperately needed for this OS were additional codec support (.flac, .ape, etc..), viewing of file directory structure, and NO ITUNES INTERFACE/SYNCH. Well, after three years nothing has changed. Enter Rockbox, third party OS that's constantly updated and actively supported. Offers the same files views by tags AND directory structure. Best of all, no crappy databases to be corrupted from a bad iTunes synch (time to reload all of your media back onto your device), and drag and drop convenience! Note that none of the newer 6th gen+ iPod have this support (as of now).
Overall, I'm thoroughly impressed with this portable media player. This baby has been used and abused the last 3+ years and still keeps on strong. Coupled with lots of available modifications that can grow with you, this is a clear winner.