Really ridiculous.
I think transparency, as a whole, has gotten out of hand, to be honest. People in office are, among other things, people, and when somebody emails them with personal thoughts, they don't expect it to published (and it's nobody's business). I understand the need, but I'm not convinced that this solution is better than not having it, especially because it's trivial for smart crooked people just to use other modes of communication when needed. (Of course, there are dumb crooked people, too). Even if Jeb hadn't released this stuff, anybody could have asked for it under a sunshine law (although not with SSNs, presumably).
Hopefully it slows him down, some. Individually he's not the worst candidate, but we need no dynasties in this country.