Get a software program that can record from the Line-In jack. I like a program called AudioGrabber. Attach your stiletto to your PC line -in via 3.5mm audio cable. Start playing the clip and hit the Record button on the software. It should only take about 4 hours to record...
(BTW, There's no way to transfer the files off of the Stiletto, they are encrypted per device.)
I record from my S2 to my computer using the Xitel `Record from your stereo to your computer' system. This system was $80 at BB, and was slightly cheaper at Sam's Club.
The Xitel IS a USB interface. Part of the expense is the interface box that converts the audio out from your stereo (I'm using a headphone jack and it works great) to USB.