Politics is kind of like teaching: Everyone has seen the job being done, and most people are pretty sure they could do better. The reality is that politics and teaching require a very definite set of skills and knowledge, and newcomers to both professions are often overwhelmed by all the stuff they didn't know, not to mention the stuff they didn't know they needed to know. Complete novices are in even worse shape.
Rookies to the federal government are constantly running afoul of all the arcane rules and minutiae they don't know anything about. That's why every administration has a staff of compliance people, ethics consultants, and rules consultants. From his history as a businessman, it's clear that Trump cares nothing for courtesies and protocols (except when he thinks someone else has taken a shortcut against him), and his equally inexperienced staff takes their cue from him. No rules. No customs. No traditions. Just do what you want to do; you're important and what you say, goes!
Now that the administration has been installed, some career political hands are slipping in, handling some of the stuff that the campaign staff knew and knows nothing about. I'm sure they're appalled. Can this Augean Stable be cleaned out short of re-routing the Potomac River? How long will the pros' dedication to professional politics withstand the instinct for self-preservation? Every time a non-campaign staffer leaves the White House these days, you have to assume they came up against something so bad that they didn't want to risk hanging around anymore.