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Ones I've regretted:
Just about every PDA I've ever bought (the exception being my first - a Psion Series 5)
Every compact camera (film and digital) I've ever bought (including the Canon G10, but that one is the one I regret the least)
Every portable non-mp3 music player
Ones I haven't regretted:
My Apple MacBook (or the iMac before it)
The Olympus EP-1 camera
Any of the Canon SLRs and DSLRs I've had
My iPhone
My PRS-505
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