(2) Dan and I are part-time angels really, with very small checks given to a very small number of companies. Also, as sama mentioned, we basically stopped investing at all once we got into YC. We still make an investment from time-to-time but mostly in people we know already. We don't have meetings, way too busy on Standard Treasury.
(3) We felt like an underdog when we applied to YC. I think we were underdogs when we applied! We didn't know them and certainly didn't have much of a reputation outside of financial technology (still don't?). We felt very fortunate when we got in. YC was amazing for us and has always been supportive of our mild madness.