I feel the urge to ramble on this topic.
Thoughts: It is very late in the game and many experienced players honed their skills and built their assets in a more charitable time. Kremen got Sex.Com without even paying a reg fee.
It used to be possible to build Page Rank with a few bucks. I once had an email spider before spam was considered evil or illegal, and hosed traffic at sites with cute little newsletters full of links. I pumped sites up to PR 4 and 5 with modest investments in Google clicks that I bought for a nickel a piece. Those clicks now cost $10 - $15 for legal terms. I'm outta that game.
Meanwhile selling clicks to Google has gotten harder and harder.
Parking used to make good money -- not that it ever did for me. Affiliate programs used to do better. Now there's competition crowding in every day as the economy pushes more people online to try their hand at any web-scheme they can get their hands on.
As a result, domain valuations have fallen, people are winnowing out their holdings, and I'm noticing when I let stuff drop, nobody even picks it up. I keep getting solicited to buy the dot-com of every dot-net I own, and the other day I did break down and get WhiteHatLawyer.com for $99, because I'd wanted it for ten years. And that's what it would've cost me to have it registered for ten years. Of course I would've used it, but I've got it now, and I think it's a good deal. Meanwhile, I'm chucking the rubbish that I don't care about. When nobody picks it up, I realize it really was rubbish.