Q - As much as I enjoy using Apple products, I absolutely detest iTunes. I come from a generation of Winamp and Media Monkey, where monitoring folders for incoming music has been built in for ages. For some reason, iTunes doesn't have this. It drives me nuts having to drag new music into my iTunes everyday if I buy it from Amazon or some other online store. I also don't want iTunes to manage my music. I have my own folder organization already, thank you very much!
A -Yes! Someone out there has similar sentiments towards iTunes!
Luckily, we've found a solution for your problem. That is, unless you own a Mac. If you own a PC, however, you are in luck.
iTunes Folder Watch to the rescue. iTFW allows you to set up Watch Folders and to quickly evaluate whether there are any new iTunes-compatible files in any of them which do not exist in iTunes already.
You also have the option to add them selectively or fully automatically (requires an annoying fee). In fully automatic mode, iTFW will add to media in the background and show an indication that it has added the songs to iTunes when completed. You can even create playlists for each individual watched folder, too (a pay-for option included with the fee).
I went ahead and gave it a go and now find myself using it daily. The interface and icons are fugly as hell, but hey, I won't complain when functionality works so darn well. Highly recommended for the lazy media collector.