Very possibly. My sad admission - I am only loosely familiar with the Star Trek Mythos - and have probably seen less than 15% of it's available content. What I do know, is that Wesley was this badly introduced character - who was supposed to be great and beloved - but was disliked by most viewers because Roddenberry liked him too much and was too generous in his introduction of this character.
Therefore, to amuse viewers, Wesley must pay.
So, some circumstance would require him to have 'career enhancing training' using the holodeck - including some rather merciless training provided by a hologram of Dr. Gregory House. In which all of the flaws in previous Wesley writing would be seized upon in a very meta fashion by Dr. House. This would prove upsetting to Rodenberry but cathartic for viewers.
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timeasmymeasure
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Therefore, to amuse viewers, Wesley must pay.
So, some circumstance would require him to have 'career enhancing training' using the holodeck - including some rather merciless training provided by a hologram of Dr. Gregory House. In which all of the flaws in previous Wesley writing would be seized upon in a very meta fashion by Dr. House. This would prove upsetting to Rodenberry but cathartic for viewers.