Outcome: "Win"
Record: 119-10
Streak: Won 1

Summary: I broke my Wednesday-loss streak, although I got a loss yesterday, so I didn't really do any better. Yeah, the problem Dan points out in his response below is one of the fundamental problems that any "system" must deal with. I tried to give my best account of how I deal with it, and I encourage any critiques of my method.
So today I set a challenge for myself. It's not moderate, so I'm violating one of my core principles, but it's not a critical component of my plan--it's totally for fun--so it's not important that it violates my principles. My challenge is 100 straight wins. Today is #1. 100 would put me right around Boston/Philly time, which would be an amazing way to carry me into that transition.
I was thinking tonight that one effective way to use the blogs would be to "sponsor" each other. I tried to do this by offering Dan a raspberry mocha if he got five straight "all 1" days. The awards could be based on actual project milestones, like, I'll do x once you reach stage y in project z (or I'll do x if reach stage y in project z within a given range of time), or the awards could be based on our personal rating systems, like mine was when I attached it to Dan's rating system. I would think that pure monetary value of the incentives should not be the focus. It should be more creative. Like, Dan might say, "if you get an A in both of your classes this semester, I will promptly read any book you recommend to me, and provide feedback"--something like that.
I will try to set the tone: Dan and Derek suggest May as the time when they think their shit will be blowing up. If they simply complete the core program before March 31st, I will contribute 20 uncompensated data collection hours, and for each day earlier than that, I'll add another hour. By core program I mean everything except the content. It must be online with at least some sort of initial content and the capacity for users to start creating accounts. Does this seem too hard or too easy? Let me know, and I'll adjust my offer. I was just trying to think of something to test the sponsorship concept.