Well, 'The Courier' is purely fictional. The plot and characters were imagined by the writers for entertainment purposes. There's no real-life basis for it.
I don't know. It might have elements of truth or it could be completely fictional. You'd have to look into the background and author's statements to know for sure.
Not really. 'Courier' is mostly a fictional creation with elements that might draw inspiration from various sources but not based directly on a specific true event or person.
In some fanfics, Courier 6 finds Benny in a seedy casino in New Vegas. Courier 6, being the tough character they are, might walk right up to Benny, guns blazing, ready to settle the score. However, Benny could try to talk his way out of it, offering some valuable information or a share of his latest scheme. This would create a tense and exciting encounter full of dialogue and potential double - crosses.