I feel like YDN is pretty meaty. And yes, 'Let Doug do what he wanted and paid him, and gave us Hadoop and Pig with great docs, along with YUI' is a pretty strong contribution.
I've never worked there, but if I could work on a cool project - yes, I would.
You do sound like you have a unique perspective :) I've always heard nothing but bad things about Yahoo management, and if they acquired my baby and kilt it I'm sure I'd hate them too. Don't the cash and freedom make up for it, somewhat?
Can't you work on anything you want now that you have the money? If you hadn't sold and some catastrophe struck you, what then? I'm sitting here counting out months of savings and wondering if I'll be able to build what I want to build before debt and daily life grinds me down.
He wasn't broke before the acquisition. A really successful product means you kinda get to do what you want whether you get an "exit" or not. Sure, the big cashout means you can go on a long vacation or something...but how many of us are in it for a long vacation? If I were to sell my company today, I would be thinking about what my next business would be by tomorrow.
A really successful product is not guaranteed to remain so, but cash remains cash. I speculate that if yahoo was going to get into social bookmarking then if he hadn't sold, they'd have picked up somebody else and the competitive landscape changes drastically. To me, the big cashout means an opportunity to work on bigger projects. The personal financials are of course the most important factor. If I had a few million or a fat trust fund, I agree selling only makes sense if I figure I am getting a very good price.
Remember that many people do not have either cash and freedom OR a big popular project. While nowhere near the level of Delicious, I had a project acquired, and ended up with neither cash and freedom or a project to work on in the end. But, I'm not ready to say I wish I wouldn't have sold it. It's part of learning and I'll have a different perspective next time around. So, while I know where you're coming from, I'm not going to feel too bad for you ;-). Seems like you'll now nkow what to consider next time.
BTW, I still use Delicious every day, thanks for creating it.