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The way I look at it: If this thing (whether it's an ebook reader, a computer program, or just about anything else) did what I wanted it to when I bought it, and if I found its price:utility ratio sufficient at the time, why get stressed out because there's something better available now? It was good enough to buy back then -- so unless it's quit working in the interim, it's still good enough. If I pay $200 for something, it's because whatever it's doing (displaying ebooks, in this case) is worth $200 to me. If having ebooks displayed to me, along with whatever other features the device has, is worth $200, then no matter what happens, I just remind myself of my original purchase decision and, usually, I'm satisfied. That happened with my netbook, by the way. It's an EeePC 901, and they dropped the price by $100 about six weeks after I bought mine. Okay, so it was cheaper ... but I thought my lil' kneetop was a good deal at the price I bought it at. So I was (and am) still happy with it; no buyer's remorse. Now, ASUS essentially dropping support for Linux, that ticks me off, but that's a different matter. (and yes, I'm gonna put Eeebuntu on it once my life is done whirling around)
I, too, have a Sony 505. When I got it, I picked it because it did exactly what I want, and it did it the way I want it done. So Sony makes newer, fancier, more feature-filled devices now ... and? My 505 still does exactly what I want, and it does it exactly the way I want it done. I am no less happy with it because there might be something else (though if there is, not from any of the "big 3" vendors) that does it better.
The only exception is when I get something which is the best of several not-so-good choices. That's a surefire remorse generator. Looking at buying decisions this way has made me less likely to get something like that, and more likely to wait until one that fits my specs completely becomes available.
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