I would like to say the 5th Gen Video iPod is still the best and most versatile iPods made. If you have the thin model that is 30GB or less, you can replace the hard drive yourself. $70-$90 for the hard drive (100GB) model MK1011GAH-there is also an equivalent Samsung for less. It will be faster, thinner than classics and your current one and will store more songs because it doesn't have the split screen menu or the coverflow that nobody uses. You can buy a better battery that will last longer for the charge and it's life will last 4 - 5X longer than what you purchased with Apple. That's the route I would take. If you already have the thinker plate 5th gen, you can add a 250GB hd with the same battery. The video ipod can do a lot more than that. You just have to look.
My 5th generation iPod Video is dying(I keep getting a sick face) . I have had it since 2005, so it has lasted me a good long time. I don't care to get rid of it, but it only works maybe once a day for an hour if I can get it to start up.