Came back to this thread during lunch, and a few things I'm seeing have me more worried about Caddy than I originally was. Originally it just seemed like a very minor misstep, but now it seems more likely to be the start of something worse.
Can I ask - what exactly is Light Code Labs? The page really doesn't say much. It almost seems like some 3rd year Computer Engineering student at BYU came along and talked Matt Holt into creating a business of Caddy? I can't see anything about business expertise, and in the wedge fork trademark issue the other co-founder just responded that he was "part owner of Light Code Labs" and nothing about development. On the site it just says this person "recently got into web development...[and] wants technology to be more intuitive for people to use".
It might just be my dislike of fluffy BS, but it seems like red flags to me.