I'm not on the foundation, but I know a couple of people who are. If one of them shows up, he or she will have better answers.

• No, and Damian and Dan may or may not receive a grant this year. I don't think it's been decided.
• I don't know. You may need a parent or guardian to sign for you if you receive the grant.
• Yes, most new grants will probably be small ones. There should be a handful of grants announced in the next little bit — perhaps in the next few days, or perhaps at YAPC::NA. In this case, "small" means "less than a few thousand dollars".
• In the past, rather infrequently. In the future, hopefully much more frequently. Some will be awarded soon. I suspect there will be several smaller grants awarded each quarter.