Cassette-to-mp3 is fine and quite do-able, though the quality does not stun me so I've only seriously tried it on irreplaceable original tapes of stuff I can't otherwise obtain. Depending on how mainstream your interests are, the iTunes music store may well be selling the songs you want. Their selection is huge, but they aren't going to have an obscure 80's British indie band. They only sell songs in the Apple AAC format, though; that works on iPods, but I'm not sure how easy it is to convert them to mp3. You could of course burn a CD using the downloaded AACs, and then rip mp3's off that mix CD, and plenty of people do; it's just a bit of a pain. I also regularly buy one-hit wonders from half.com just to have the original CD, or if it's not available on iTunes.
I am a huge fan of my iPod, because I have very flighty musical tastes. I want to listen to one band, and then a few songs later I really really want to hear something different, etc... so the ability to have ALL my music with me is amazingly useful, and for that one needs a multi-gigabyte music player such as the iPod. I used to carry a big CD wallet, exposing my originals to damage/loss, and even then, only having 20 CDs along often meant I didn't happen to have what my impulsive ears wanted next. The main disadvantage of the iPod is that it's relatively expensive, but in this case I think it's worth it if you listen to a lot of music. I could play this thing for a full week without repeating once, and it's only half full. The user interface is beautiful and intuitive, and I can find any of my 2500 songs in a few clicks.
The cheap mp3 players with Flash memory hold a LOT less, which I guess would mean you have to make up "mix" Flash cards, similar to mp3 CDs. This is exactly what I was trying to get away from, so I'm an iPod person all the way.
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I am a huge fan of my iPod, because I have very flighty musical tastes. I want to listen to one band, and then a few songs later I really really want to hear something different, etc... so the ability to have ALL my music with me is amazingly useful, and for that one needs a multi-gigabyte music player such as the iPod. I used to carry a big CD wallet, exposing my originals to damage/loss, and even then, only having 20 CDs along often meant I didn't happen to have what my impulsive ears wanted next. The main disadvantage of the iPod is that it's relatively expensive, but in this case I think it's worth it if you listen to a lot of music. I could play this thing for a full week without repeating once, and it's only half full. The user interface is beautiful and intuitive, and I can find any of my 2500 songs in a few clicks.
The cheap mp3 players with Flash memory hold a LOT less, which I guess would mean you have to make up "mix" Flash cards, similar to mp3 CDs. This is exactly what I was trying to get away from, so I'm an iPod person all the way.