Have you used an agent before? Their whole business is about helping individuals and businesses pick plans. My agent has shown me some good data sheets that get close to giving you apples to apples comparisons. I bet you could borrow a lot from their business models.
It would be cool if I could see my existing plan on there and be able to compare apples to apples. They keep raising my premium, it would be nice to know if there was something else out there that had a lower premium.
I know there are a lot of hackathons happening out there. Does Hackathonia aim to be a platform to launch and run them? I think there could be some useful tools around hackathons, helping organizers organize and promote them, helping teams get involved in as many as they want to get involved with, or helping sponsors find a hackathon to sponsor that suites their mission. From the page you've got up now I'm not sure who you are aiming to help or how.
We did some interviewing a few weeks back. I'm looking forward to the piece, the interviewer was pretty in touch with the current goings on. Let us know when it's going live if you guys get more details.
Something that helped or encouraged people to get the word out about the meetup to interesting, useful, and active people would help. "tweet this" or "post to your Facebook wall" might do the trick.
The Chicago meetups have been really good. The more recent ones are getting slightly less turnout but are still a great way to spend an evening.
In terms of features/tools to help organize, there's a lot of multi-person messaging back and forth that goes into getting a meetup scheduled, something that helped the group settle on questions like time/date and venue would be useful. I'd be careful about going too far into automating the process, you risk loosing some of the engagement that gets people aware of the meetup. I could see extending the Hacker News' site's up-voting system to various choices for time/date/venue working well for this.
I made it out to the Awesome Found's Visualization content party. The event really drew out a great crowd, artists, entrepreneurs, scientists, etc. I hope the ScaleWell events can do something similar!
ScaleWell seams to me like a more direct action form of a Y-Combinator or TechStars incubator. It's something that's easy for a group to set up and start helping startups move forward. (Full disclosure: I'm a trustee)
It might even be a little limiting that the people getting the $1000 have a project that they intend to work on with the grant. What was the best return the Stanford class got with the $5? $800 in 2 hours?