I'm perfectly willing to over pay if it's *what I want* and it's normally unavailable. I looked for a Rosso Corsa for a *really* long time before I found Rosie in rough condition. I paid $500 more than she was worth, and was happy to do it. After going through her, I wouldn't take $1000 more than I gave.
I had been looking for a Lario for a good while, too, and gave more than it was worth when one became available. At my age, I don't have years to wait for another to show up.. Naturally, since then, I've seen a better deal on both, but I've had some wonderful experiences that I wouldn't have had.