The White House New Media team circulates multiple highlights each day of what people are looking for online - Twitter trending topics, popular Google searches, etc. - and it gives us a sense of what's breaking through, what isn't, and a sanity check for what the larger online population cares about at any given time.
I think it will be very challenging for someone who has not been in prominent public life in the age of Twitter to go out on the campaign trail.
There is no business model in the modern media that promotes comity. If we worried too much about criticism, we wouldn't get out of bed in the morning.
As I understand it, triangulation is the idea that you demonstrate to some set of swing voters that you are politically palatable by poking the extremes of both parties in they eyes.