well Jay, while you were a wall flower in that time frame some of us bought houses and did pretty well. when i bought my house i thought it was overpriced, but was a bargain given the market. now i'm astounded with what my house is "valued" at. heck, even the property+building taxes have far exceeded the value that we paid for the house.
but fortunately for you i don't frequent these East coast social dinner circles you mention, or else you'd have to hear me go on and on about my squalid little hovel whilst sipping the chardonnay and eating all the mini-hotdogs.
I actually DO feel like I'm glad I bought when I did, or else I WOULD feel priced out of the Seattle housing market. Its going to have to correct quite a bit more actually before it is back to a level where I think a home is a relative value as compared to what I paid way back in 2002 (or was it 03, I can't remember now).