I pay a premium price for new tech that I really want. (like my PRS -300 for $379) or as a gift. Then I upgrade mostly when the price is right. For example I bought my roommate a PRS-350 as a gift for $199 but only bought myself one when the price was $50.
I would not have bought a T1 but my roommate bought me one as a gift. I like it okay but don't see it as a significant improvement.
I did buy a car once,, but found that life was not significantly improved. I would find myself taking a bus or a taxi or even walking because it was simpler than finding parking and cheaper than paying for it.