Why will iTunes v. 8.0.2 not load my songs to my iPod Classic 3rd generation ver. 2.3 using OS 10.5 ?

Problem: iTunes does not automatically transfer my songs to my iPod.

I have an iPod Classic 3rd generation v.2.3, it has a 20GB capacity, I'm using iTunes 8.0.2 and am connected to a Mirror Drive Door 1.25 GB DP running OS 10.5. I am using the Firewire Dock to communicate with my Mac and to charge/power my iPad.

It has a bad battery, however, it still holds a charge. I've been able to reset the iPod. I do not have the installation disk. The iPod does cause iTunes to open. The iPod shows up in the iTunes sidebar. It shows that it has checked for updates. However, I'm using a dial-up connection and thus, it will not finalize a connection with Apple to do the RESTORE. My problem is that according to the manual any songs in iTunes will download to the iPod automatically. Well, it does not do that. In fact, I have seen no evidence that that downloading process has ever been initiated. I have connected the iPod at least a dozen time with the the dock plugged in when placing the iPod into the dock. I've also plugged the Firewire connector into the port on my Mac with the iPod already in the dock.

Am I missing some step or some setting that I have to do manually for the transfer from iTunes to the iPod to take place?

Anyone have any ideas, I would appreciate assistance from my fellow Mac compatriots for your help with this problem.