"Stupidly bypassed a TON of domain names thinking "naw, they'll be around for a while" since at the time I was too cheap to register them -- it was Internic at $70 per year at the time "
No Shit !
I had casino.com and bank.com com way back and let them expire. That was when you could register hundreds of domains and not pay the invoice if you changed your mind.
Big Mistake !
I was also the first paid advertiser on ynot and the second on websidestory back in the day
Andy at lips.com made a killing on the front page of websidestory. I think he paid 2K per month and was making 60K