This program has a lot of potential, and is packed with features compared to the other ipod rippers out there. The interface is fairly well thought out, and is not just a window and a couple of buttons like many other similar applications. The UI is very nice. While I've never been a fan of the brushed steel motif (I think it goes against Apple's original usability guidelines), it is consistent with the OS, and this app does a good job. Everything is well laid-out, and there's a lot of detail here, but it is not cluttered.
However, and here is its real downfall, it is not a very stable application. Every time I've used it to transfer songs to my iTunes Library, it crashes. (OS 10.4.2, iTunes 4.9) I don't think it likes to copy more than a few hundred songs at a time, as it seems to be more stable in that instance. Of course, every time it crashes reduces my trial period. One other thing I don't like about the program is that the UI feedback when you copy could be better. Many times it seems like the progress bar isn't moving at all, and you aren't sure if it has frozen or not. It would be useful to provide more granular information about the copying progress.
So, although iPodRip is definitely the most feature-packed and usable of the ipod ripping applications out there, frankly I would not spend money to purchase this product until it becomes less crash-prone. If this product were stable, it would be worth the $15 shareware fee the author requests. But right now I want something that doesn't blow up when I ask it to perform its main function.