Seems that others are having the same problem. They click on the file, hold shift, then press delete, then confirm it to go to the recycle bin, and it so far has worked (for me anyways). I find that to be a bug. It should delete when I select it to go to the recycle bin, not when I press shift delete.
A also notice that it immediately deletes the file to the recycle bin using shift delete rather than hesitating and freezing for a few seconds using only the delete key. Weird...
I have somewhat of a pet peeve with iTunes since I like to have my computer as clean and clutter free as possible.
I download many podcasts from various sites and listen to them and watch them when I have free time. After I am finished, I right click on the one that Im done with (or ctrl click on multiple podcasts) and tell it to move the files to the recycle bin. The thing is, many times I still find that the podcast is still in the folder within the iTunes directory taking up space! Its not shown in the podcasts within iTunes because I deleted it, and Im sure that I always click to have it removed to the recycle bin (not "keep files"). Even though I do that, sometimes they dont always delete!
Is there something wrong with iTunes that needs to be fixed?
I am aware that I could possibly tell iTunes to delete all podcasts that have been "read" or viewed, but I prefer to do this manually.
For now, I must go through each folder and manually delete the files.
The only thing that I may not be doing is emptying the recycle bin immediately after every time I send the files to the recycle bin. My only assumption is that iTunes sees that I havent emptied my trash, so it leaves it??? Either that or it screws up, I dunno.
Chowhound
Comic Vine
GameFAQs
GameSpot
Giant Bomb
TechRepublic