1. Music Store Compatibility
What online music store will you be using? Is it Amazon, Rhapsody, or Yahoo. If you want an Ipod there is really is ONLY one choice and that's Itunes, however if you want a cheaper MP3 player that is a little more compatible then do your research. Maybe you like Napster's interface of the subscription service that Rhapsody provides. Either way go to the website and make sure that the device you are buying works with the music store. Otherwise you will be very heated when you find out that there maybe issues with your Sandisk Sansa and Real Music Store, just as an example.
2. Do you need a Flash MP3 player or HDD?
Companies generally make two kinds of MP3 players Flash memory (also known as solid state) and HDD. The latter can come in Micro drives like the Zen Micro or just a small Hard drive like the Ipod. If you are going to use the MP3 player to work out with then you need a Flash drive. A hard disk actually works like a small CD player and the running, jumping, or whatever you're doing will cause it to skip or even stop working. Additionally if you're pretty rough on your devices (take a look at your cellphone and count the number of bumps and bruises) then you'll also like to go with flash. The only issue with flash memory is that it's more expensive and right now tops out at 16GB. The 30 & 60GB MP3 player that you see are all HDD.
3. Want to watch TV shows on your device too?
Some MP3 players can really do alot. Ipods are able to play music videos purchased from Itunes along with other video content. Creative's Zen Vision M is compatible with the Tivo service and will let you watch recorded TV shows on your player. The thing is the world of video is 10 times more confusing than audio so do some research here and determine where you will be purchasing/downloading your content.
4. Keep your hearing healthy
In all honesty the earphones that come with 99% of all MP3 players are really bad for your ears. The test to use is if you can only really hear the music at 75% of the max volume the current earphones could be effecting your longterm hearing. Consider in-ear phones or earbuds. They allow comfortable listening at a low level (even for you hip-hop fans). It's worth it to spend 50 bucks on some decent earphones to keep those ears safe.
5. Size matters!
I'm not talking about physical size of the player here I'm talking about size of the memory. People can try to sell you on a 512MB or 1GB of memory as more than enough but keep in mind that MP3 players are pretty addictive and you may find yourself needing more space like me just 2-3 months later. Also don't believe those numbers that every song will just be 5MB so 1GB player can easily give you 200 songs. There's this thing call bitrate which effects how good your music sounds and you don't want to go below 128kbps that's the quality of radio. Many equate 192kbps with CD quality. I would estimate that each song would run about 7MB which means that your 1GB player can only hold about 140 songs not 200. That's a substantial difference.

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