Hi Tech 101: The (i)Pod people

There's one thing they forgot to tell you - where to get the music to fill it up with.

So you got a new music player for Hanukka? Welcome to the ranks of the "(i)Pod people" - those who get to have the soundtrack of their lives accompany them anywhere and everywhere. Finally, you get to be one of those unflappable people who never have to lack for entertainment, no matter where they are or what they're doing.
There's one thing they forgot to tell you about digital music players, though - where to get the music to fill it up with. It turns out that getting your favorite music in digital format requires you either to have a significant disposable income - for spending at on-line music stores from which you download music - or to compromise your ethics by surfing to a file-sharing site and downloading music illegally. And while there are a million and one justifications for doing so - the record companies make enough money, everyone else is doing it, etc. - you may still not be comfortable with the idea (http://www.riaa.com/).
Fortunately, though, there are perfectly legal ways for you to get the music you want in digital format - for next to nothing. Of course, as with anything else in life, there are two ways of accomplishing this goal - the hard way and the easy way. Never one to shirk hard work, but lazy enough to want to get out of it, I hereby present both methods:
The hard way
If you've still got cassette tapes, you may still have a tape player - like a Walkman or a "boombox" (you can still buy the latter in some electronics stores, believe it or not). To that, add a 3.5 mm. (1/8") male-to-male stereo connector (available at places like Bug Computers); plug one end into your computer sound card's Line In, and the Line Out (if available) or headphone jack on the music player.
Once you've set up the physical connection, it's time to start transferring the music. While there are many programs that you can use the best (and free-est) one is called Audacity, which you can download at http://audacity.sourceforge.net/. Audacity has a wealth of features that let you record in low, medium and high quality, add special effects or emphasize the bass or treble, etc.; it even has tools to reduce the infamous "hiss" that accompanies cassette recordings, a sound feature you don't get with CDs or digital downloads.
Once you record and edit your music, you can save it into WAV (CD) or MP3 format, compressing the music file as much as you need to. You can even use Audacity to record audiobooks, record from your TV, record from a record player (!) or even use it to make ringtones.
Audacity is very well documented, and there are tutorials galore that guide you step by step in a host of audio projects. It may take some work, but converting your cassettes is a guaranteed way to get high quality music without paying any more for it - and you may just come across some golden oldies that haven't even been converted to digital format yet.
The easy way
Recording your old cassette tapes to digital format is a great way to get the music you want into a format compatible with modern equipment, but it takes work - and work takes time. And who has time these days? But you still want your cassette oldies - for free, preferably, without entering the ethical jungle of illegal downloading.
Fortunately, there is a way for even the overworked to legally build up their music collections, of any genre - for free, with almost no work at all. The big secret is at http://www.stationripper.com/, where you can download StationRipper, which can get you as many as 6,000 new songs a day off streaming Internet radio. StationRipper performs this little miracle by connection with Shoutcast streaming Internet radio (http://yp.shoutcast.com/), where more than 10,000 streaming Internet radio stations await your attention. The stations include any musical genre you can imagine, and many of them stream their music in good quality stereo (unless you're a real expert, the 128 to 160 kbits/s that many stations stream will sound as good as CD quality to your ears).
StationRipper keeps the sound files separate, tagging them with the name of the song and artist, and even avoids recording songs you already have in your collection. The basic StationRipper is free, but you will find it such a valuable tool you'll probably want to buy the extended version for $19.99.
Building up a music collection with StationRipper is even easier than downloading music from file sharing sites, since you don't have to go looking for the music - it comes to you, free and legal. And if you happen to run into a chatty deejay speaking over your favorite song, just rub him/her out with Audacity. But not to worry; with more than 10,000 Shoutcast streams (not to mention streams from other services you get with the extended StreamRipper), you're guaranteed to find plenty of high-quality music to fill up your new music player with. And with so many stations streaming so much music, the law of averages guarantees that you will get the music you really want faster than you can download it from a file sharing site.