2. I tried to work part-time the first year. It's a bad idea. You can't do two things at once.
3. It's difficult to measure this because the site is seasonal. The first year was OK but I had to wait 8 months to see the improvement. I started making a non-negligible amount of money the second season, August 2006.
4. Yes to all 3. Obviously the most important thing is to start developing. My only focus this whole time was to make the best product. The ad money will come later. (This isn't true for all startups. Fantasy football players comprise an unusually lucrative advertising demographic.)
5. It's tough. I was pretty much on my own. I read this somewhere: "In a startup, nothing happens unless you make it happen."
6. I'm pretty stable but you can definitely go insane working alone all day every day. I don't have any advice on how to cope with this. No startup is easy.
7. I have unwavering confidence in what I am doing. I received very positive feedback almost from the first day. The site was profitable so I could have kept going indefinitely. Also, this is definitely a dream job. Fantasy applications are interesting from a comp sci perspective.
8. I was approached by AOL (and others).
As for YC, I applied and was accepted right when the AOL negotiations took off. So I decided I couldn't do YC at that moment.