The folks behind VersionPress did a postmortem on what they learned running a crowdfunding campaign. They got less than half of their goal, but learned a lot and still managed to utilize the funding they did get. If you’re looking to crowdfund a project, you should probably read this and any other case studies you can get your hands on.
In short, they’re glad they did it:
However, I still think that the crowd-funding campaign was one of the best ways, if not the best way, to start the project. It was an awesome experience and it truly “kick-started” VersionPress. What more could have we hoped for?
Jeff Chandler also covered this today, and in his post he links to an episode of WP Weekly where he interviewed three WordPress crowdfunders — another good resource.