Kirk was certainly the biggest Prime Directive breaker of all time.
That's how the 'Cowboy Diplomacy' thing comes about. He seems to honour it more in the breach than in upholding it. He sees it as a suggestion to be left up to his discretion, but it is definately an order -- General Order Number One. There are numerous examples of him breaking it, which I put in another thread.
Archer will have no such problem, as Starfleet had not yet instituted the prime directive until after at least 2168 (the time that the Starship Horizon visited planet Sigma Iotia II (Piece of the Action)
Picard was the strictist in upholding the Prime Directive. He even goes as far (Symbiosis) as refusing to reveal the truth to a population, enslaved by another by addicting them to a drug.
In Ensign Ro the Federation is accused of hiding behind the Prime Directive. By not "getting involved" in civil wars, they can claim the moral ground, even when there is a clear right and wrong.
Janeway talks a lot about the Prime Directive, but has often broken it too if it suited her. She has been much more complex in her attitude to it.
I think that distance from the centre of the Federation, and superior officers has a lot to do with it. Kirk was on the edge of the final frontier, Janeway is in the Delta Quadrant, whereas Picard is in daily contact with Starfleet Command.
I really like your idea of Prime Directive breakers getting faster promotion though. That does seem to be the way to get ahead.