Man, I wish I had the foresight to get into this Internet thing way back then. But I was in high school and, well, I didn't know any better. Sigh. If I could go back in time... "So, ah, you guys are starting a company called Google? How much can I invest?" "Amazon? Sounds good!" "Yahoo? It sounds so strange it must be true!"
Something like this happened to me a few years back, where by accident a domain of mine expired. I was so pissed because I had about 100-200 backlinks, nothing major but the name meant alot to me. So, I went and changed all of the backlinks that were pointing to that site away from it. Now I look back and still the person is running ads on the domain, with no links to the site anymore.
Today there are many services that allow you to watch for expired domains and try to overtake them. Many webmaster are hunting for those with high Google PR. The easiest way is to buy those who has some restrictions as to who might purchase them. For example to buy .fr domain you must be French resident so if you are one it is easier for you (less competition) to overtake such. Back then there wasn't so much competition and no ready services, so it was easier if you interested in buying expired domains. But also harder to monetize them.