Right. back on topic.
I think i know exactly what SuperTyphoon is trying to do, and it won't work for a specific reason.
Using ***, SuperTyphoon, are you trying to drag and drop from inside the *** database? as mentioned before, this won't work. what wasn't mentioned was the reason, which i am almost certain is ***. *** is Java written. this means that the code is wonderfully crossplatform, and requires very little work to be cross-platform. the downside is that i's clunky and amateurish in appearance and functionality. this also means that drag and drop doesn't work to how you would want it to (ie from within a Java environment to a Windows environment and then into a largly mac-based environment.).
there is, however, simple solution. in the library section of ***, is a button lableled 'explore'. clicking this will open the folder in which the downloads reside. now you can drag and drop happily, and the next time your ipod is connected, auto-sync will transfer this new song across.
perfect. (nearly) the point is that this is a Java issue (i don't like Java much), not an iTunes issue. iTunes is doing exactly what it's meant to do.
if you want even better functionality, use the iTunes Music Store and pay for your bloody music.... you get full syncing, full, high-res artwork and perfect Tags.
but i wouldn't condone that sort of thing. i've recently stopped using ***. i don't like priacy.