Trump's "tell it like it is" speaking style has gotten him to where he is now but there are times, particularly after major events, when he really needs to sit down and carefully craft an articulate response.
Your two examples are times when Trump left me scratching my head wondering, "did he really just say that?"
Yes, that is a factor that keeps things interesting.
Were people congratulating him after the Orlando shootings? I think they probably were, that hey Donald you were prescient about a problem. But true, sometimes being sympathetic means more than being right.