I've heard it said by Dave Winer and many many others: if only Dean had reinvested half the money raised into the Internet, then ...

OK, so you're the Dean Campaign Chief Information Officer in August 2003. The money starts to roll in. $20 million over six months, $2-4 million per month.

What would you spend the money on?

1. What does your monthly budget look like?
2. What is your application and infrastructure portfolio?
3. How much will you allocate to maintenance?
4. You're building from scratch, so what problems do you hope to avoid through wise architecture?
5. What are your big milestones?
6. Who are your key vendors?

How do you spend in consonance with the campaign strategy?

1. How will you use the Internet to bring offline voters into the campaign at the same numbers as radio or television broadcasts?
2. What is your online strategy for responding to attack ads and opposition pundits in radio, television and print?
3. Online community takes time to build and is very hard to organize geographically. What will you do to match the state-by-state primary schedule?
4. What can you do with online services to serve the campaign in caucus states?
5. You are preparing for Bush to launch in Spring 2004. What are your countermeasures to reach out to moderate Republicans online while the GOP uses its advanced voter email systems to barrage 200 million validated email addresses?
6. How will you lower the cost-per-vote vs. the GOP?

Uses Ajax and some other web2.0-ish features.