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The iMac...I don't regret for a second. It was so intuitive, and such a pleasurable change from so many career years in front of a Windows PC. It always feels welcoming to my photo organising and post-processing.
The Iliad...I kind of regret that. The eInk is good, and I empathise with its popularity, but its emotional response from me is simply...grey. Its (relative) slowness, its screen-refreshing, its screen "colour", its occasional bugbears with dictionaries, its drab unattractiveness (oddly, its relatively limited battery time doesn't bother me in the slightest) just feels like it sucks some of the pleasure - the pleasure I've got with the obsessive books-consumption that started in childhood - I get out of books and reading. It's probably partly why I still buy pbooks.
Olympus 770SW...I regret. Certainly a good camera I'd recommend if appropriate, but a "ruggedised" P&S that I didn't need and didn't like the resultant photo quality of (and should have known that before I bought it).
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