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iPod/iPhone Universal dock. I never used it much at it's intended location and soon after ended up with an iTunes server sending out music from a central location instead of docking an iPod or iPhone for music. A better option would have been an Airport Express for similar $.
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I've never really made a purchase that was truly regrettable, but I only kept a 2010 13" MBA for a couple of months. Not a bad machine, but with only 2GB of ram, it was too limiting. I later found a good deal on a 13" MBP that I like much better.
Don't like the Magic Mouse
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Shortest? Hmmmm…
iPod mini? Got a deal on a used model, didn't do much for me. Smaller than the regular iPod, but still had a spinning drive, and was lower capacity. The nano line (circa second/third generation) was a better product in every way. Apple's very slow incremental updates meant to capitalize existing product sales and protect profit margins sure is good for their bottom line. Not so good for me. Swapped the mini out for a 4G iPod after a week. Loved that guy until is inevitably died about three years later.
Had a Mac Classic for a very short while (less than a month?) before realizing even the crippled Mac LC II was a better buy.
Unibody 17" MacBook Pro was a relatively short lived adventure. After finding out how expensive it was to fix even the smallest ding, I flipped it in less than a year.
I've regretted other Apple products, but I tend to stick with them for far longer than healthy to eke out some return on investment (not a big fan of either of my Apple TVs as but one example, but they still make do as lightly used gadgets for family).
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iPod shuffle first gen.
We already had a big iPod & a nano. Got caught up in the hype. But hated just having shuffle as a listening mode. Returned it a week or two later.
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Not exactly an Apple, but I bought an Umax clone in late '98 for pretty cheap after Apple killed licensing. Ended up buying a B&W G3 a couple months later when I realized that the Umax was a POS.
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The original LC. I don't think a computer had more limitations.
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PowerMac 6100/PC. Had it for less than a week (bought used, but it was a current product) before reselling it. 1995, I think.
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First generation G5 iMac. Apple sent me one replacement module after another: MB, PS, fans, inverter, and more. I had enough practice taking that thing apart to do it with my eyes closed. Finally got it stable after 3 months and put it on ebay. Ironically, I just inherited a G5 iMac from my sister and her husband,identical to the lemon had, purchased the same time as mine. It's still running strong, is now my shop Mac.