How to take music from cassette tapes to iPod So I have this large cardboard box full of hundreds of cassette tapes with music I absolutely positively had to buy in the 1980s and '90s. If I wanted to listen to the music contained on those tapes on my iPod, I imagine I could follow a process something like this:


Put new batteries in my old Walkman®
Connect some sort of cable between the headphone jack on my Walkman and the audio jack on my mid-2011 MacBook Air
Play tapes on the Walkman and record the incoming music on the MacBook Air using some sort of software.
Use iTunes Match to upgrade the quality of the resulting audio files.
Put the iTunes Match audio files onto my iPod.


I know this workflow would take a long time (each tape would have to play its full length), and I don't know if it would work.

So my questions is, what should I do? Again, my goal is to get music from my audiotapes to my iPod without having to repurchase all the tracks. The procedure outlined above is just my guess at a solution; if your answer doesn't look much like that process, but it doesn't cost much more than iTunes Match, I'm open to ideas. I'd love a solution that worked faster than my idea.
For step 3, I'd recommend Rogue Amoeba's Audio Hijack Pro which has the ability to break up the incoming audio into tracks for you and import it directly into iTunes.
But otherwise, you've got to do pretty much exactly what you planned to do.