I've started using something called PoddoX, allows (sort of) drag and drop, you put the exe where you want it, open the (500kb) program, click settings, then "Register to Explorer's context menu", and then as far as I know you just right click on a folder/song and click Copy to iPod.
I've yet to try this actual feature because my 5.5g iPoo is at apple because the battery life started being rubbish and my warrenty expires in 3 days, thought I might as well get it done by apple for free...
Also I'm not sure if it works with new iPod touch's, it works with the 3g nano and classic though according to the changelog on their site:
http://www.poddox.com/