The Touch isn’t going to offer anywhere near the storage capacity of the Classic. So if it’s important to you to have everything with you all the time, that might be the deciding factor.
Personally, I have no problem whatsoever managing the content on my 8GB iPod Touch via iTunes.
The additional capabilities of the Touch coupled with the nigh infinite expansions possible via the App Store makes the Touch the only choice for me. Yes, I can secure-shell connect to my Mac computers and gain command-line access to the Terminal. Yes, I can use the Touch to remotely control music/movies playing on the Mac. And yes, I really enjoy playing all the free games.