A naive young wordsmith from a country village must face down the dark and callous aspects of humanity to rescue his childhood friend, kidnapped years earlier, and bring down the criminal organisation which has subjugated her

This draft of the logline describes a more credible scenario and a story with more detail than the first draft. However the descriptions are still too vague for a logline and dilute the impact of the characters in the plot.

"An unassuming young intellectual?" could mean a variety of things and doesn't describe the MC in such a way that makes the reader understand how the journey ahead will be both challenging and important for him to go on. Define him as a poet, author or accountant so the reader knows what his normal state of being is. Then add a character description that illustrates a flaw such as an agoraphobe, OCD or introverted especially considering the times these would be particularly difficult to live with.

"?face off with?" is too vague a description for the main action the MC will take in the story. Better to be specific in a logline, what will he do to defeat the bad guy? Will he fight him to the death? Will he set him up to be arrested? Will he climb the ranks of the organisation and take over?

"Greatest criminal kingpin?" could be used to describe Don Corleone, Tony Soprano or Gus Fring. Problem is there have been so many of them already you really need to be specific in your description of the antagonist. What makes this criminal genius unique and to that matter an even greater obstacle for the MC?

Lastly in log lines you want to state facts about the story define what goes on not could or may happen. Instead of "?may lead all the way to the Royal Family." use "?that leads all the way to the Royal family."

"An unassuming young intellectual must face off with the 19th Century's greatest criminal Kingpin to rescue his childhood sweetheart from a life of sexual servitude and topple the criminal conspiracy which may lead all the way to the Royal Family"

"...the protagonist must find the courage and confidence to step out of his usual observer? role and act decisively, which is usually out of his character."

This is a great inner journey so best to use it to drive the story. As mentioned true to fact or not is irrelevant best to tell a compelling story than one that happened the same underlying message will come through regardless. This happens using the inner journey in a significant manner.

I still think the idea of remembering even distinct facial features many years later is not enough to prompt someone to follow a stranger around town. Also the stakes still don't seam high enough.

Perhaps to resolve both of these issues you make him bare witness to the kidnaping but due to his nature i.e his flaw he was unable to save the girl. I would also make her his child hood sweetheart or sister as appose to a generic girl to help raise the stakes even more.

Then you can structure an inner journey by which he must learn to overcome fear and become confident to stop being an observer and take action before he can achieve his outer journey goal of saving the girl. Also you resolve the potential plot hole of remembering the face of a suspect as appose to it being a significant event that confirms the man's guilt.