Version: 2008
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Tech you can expense: Get Uncle Sam to work for you.
iRiver T10 
The hunky, feature-filled iRiver T10 can play subscription-based music, but it might take time to acclimate to the awkward design and control buttons.
Rio Carbon Pearl 
The Rio Carbon Pearl largely lives up to the hype. This mini hard drive player has a great design, an excellent interface, and Energizer-like battery life.
Cowon iAudio X5 
The great-sounding Cowon iAudio X5 looks like an iPod killer on paper, but this palm-size music and video player suffers from mediocre music browsing and some key design missteps.
SanDisk m240 
With its many features as well as its compatibility with audiobooks and subscription-based music, the SanDisk Sansa m200 series is an overall great value.

MP3 player/recorder
Instead of scribbling a note about your latest business brainstorm on a napkin, speak your flashes of genius into a pocket MP3 recorder--some of these music devices also double as a voice recorder--then store it digitally. (And when you're finished, of course, your recorder can do double duty as a mobile music machine to get you through the day.) "Dictation devices are good for deductions," explains Denis P. Monaghan, a New York tax preparer. "You can go a step further and add voice recognition software that translates your voice into text on a PC." Office XP has dictation built in, but you can now use more sophisticated voice recognition software, such as IBM ViaVoice, to control your PC.

You'll also need a big memory card to store all of your music and messages. Today's flash cards can hold hours of chat, as well as your favorite bands' entire catalog, making for an audio dream come true.