I know this was never Apples intention, but with iTunes Match, you can take your analog music and convert it to high quality digital for $25. How? First, digitize your old stuff. I recommend buying an old but good quality tape player (Or record player if you have vinyl). You also need a RCA to 1/8 phone jack. You can get these pretty much at any audio store, radioshack, etc. There are quite a few programmes out there that will convert the music to mp3, a few that will label them correctly for you.
Now, sign up for itunes music match. Its only $25 a year. Not bad . What will happen is itunes will upload all of your music ( or a sample) and look to see if they already have that song in their library. You should have a list of songs that were ‘found’ and match on the system.
Now, ONLY delete the songs that have been found. What will happen is itunes will notice that your local copy is gone, and will download a digital and thus far better copy then you had from tape! Win!
The only issue on my side is I have a lot of music that is pretty unknown, so I’m only expecting a 75% match rate at best, but hey, 75% of CD quality is better then 100% at cassette quality.
Now full disclosure here, I have not done it yet. A friend of mine did and says it works. I have LOTS of tapes and my last tape player broke in transit, so I still need to find a tape player, but I’m pretty sure this is going to work. I’ll report back after I’ve converted my tape. But don’t hold your breath, I have LOTS of tapes.