CNet’s Cheapskate Blog is one of my favorite sites for technology deals and very much a daily read. They recently had this article on iPodMeister. They provide you with the labels for free shipping. You simply pack up your old CDs and get a new iPod, iPhone, or hard drive. They’ll even send you a DVD with all your music back for an additional cost (more CDs).

It sounds interesting, but I have a few questions and so did commenters:

• Legality of Keeping Your old – The biggest thought in my mind is that once you sell your CD back to iPodMeister, it’s probably illegal for you to keep a copy for yourself or use their digitizing service (I use “probably” because I’m not a lawyer.) If you it were legal to keep copies for yourselves, we’d just recycle CDs on Craigslist all day. I’d pay $2 to get the used the CD and sell it back to someone else for what I paid after I copied it. The Right of First Sale was getting a lot of scrutiny in some states as far back two and a half years ago.
• Value for Your CD Collection – One commenter pointed out that you are getting less than a dollar a CD (or less) in value when a pawn shop would give you $1-2. I’m not up on the pawn shop market for CDs so I can’t verify that.
• Is iPodMeister affiliated with Apple? – Lastly (and least importantly), does iPodMeister have an affiliation with Apple? I ask only because they give out Apple products and use a derivative of the trademarked Apple iPod name in their name. Again, I’m no lawyer, just curious about these kinds of things.

The legality of the digitizing question is the big one for me. It just doesn’t seem right. Yet it seems that the Consumerist will interview them and not ask the question. Interestingly though the Consumerist asks for feedback from it’s readers on the service (largely implying that they don’t know if it’s a great deal either).

I have a pile of CDs back from my college days (Those BMG and Columbia House “deals” really got to me.) Though I’ve digitized all my CDs, I save space by putting them in binders and keeping the artwork and jewel case in the attic – of my old home in Boston. Because the service requires the artwork and cases, I couldn’t use it even if I thought it was legal. Oh well, I think I’d rather have proof of the official rights to the music anyway.