As for who is better on document security, I wouldn't go down that rabbit hole to begin with. Have you read Assange's rationale for creating Wikileaks? The gist of it is that creating a leak culture raises the cost of conspiracies. This means that it's more difficult for any small group in power to plot against the public. So it's not really about document security, but closer to the opposite: to promote leaks so that nobody can control the flow of information.
So it's not about Trump or Clinton or any such short-sighted political machinations, but rather to ensure that nobody can get away with conspiring against the public.
It doesn't matter if the conspirator is Hillary or Flynn or whoever else. The point is to ensure that everyone is accountable. You can see how much this is hated by both sides these days, each calling the other hypocrite when they decry leaks against themselves. You can also see how those in power hate this from the Todd & Claire site, which I've seen very little press regarding.
Speaking of that, it's funny how a bunch of people on different continents coordinate with a sham of a porn site / UN "partner" to frame someone as a pedophile, but it barely warrants any mention, no? You read a lot of news, no? How much coverage have you seen? How much do you know about that? Doesn't it seem like a rather odd thing to ignore?