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(1) So, can i upload CDs without ripping?
Ripping is necessary to copy the CD’s information (music) off of the disc. Once you’ve made a copy, you can upload it anywhere you want. I’m not aware of any ripping software that wraps DRM around the music copied off disc. iTunes can, of course, rip music from CDs.
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(2) Normally, boomboxes don’t have Internet connectivity. But, can I connect the boombox to an iPad, iPod, or iPhone and have these devices access my iTunes account and play the music through the boombox? If not, how about connecting the boombox to a laptop to access my iTunes account?
If you’re talking about an older boombox, then that’s why you can burn music back to CDs and play it that way – or use the auxiliary input jack. Else, I suggest considering some iPod-specific boombox if you want access to your complete library. That latter route would also allow you to play music from streaming sources like Spotify, Pandora, I Heart Radio, etc, too.
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(3) Is the music that I purchase through iTunes always compressed (MP3 or AAC)? I wonder about the quality.
All music downloaded from iTunes is encoded in AAC format. AAC is designed to provide better quality than MP3 at similar bitrates. If you’re buying your music thru iTunes, Amazon, or any other such major name brand, I wouldn’t worry about the quality at all for 99% of us. Chances are that a true, hardcore audiophile would likely have a different opinion about any such form of lossy compression, though.
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(4) Can I use a public computer or someone else’s computer to access the music that I’ve uploaded to my iTunes account?
Sort of. You have to “authorize” that computer – it counts as one of the “5 iTunes-authorized computers” you saw in the iTunes terms & conditions. I don’t recommend that approach for “public” or other such temporary locations. Instead, you can setup iTunes on someone else’s PC to access the music library on your iPod/iPhone over wi-fi and play it that way. Then you can share your music at a party or something, but not leave a copy behind (which makes the record labels happy).