through, as a benefit of, some expressions that I too took as tough guy talk from old NY I realized were more widely distr

I'd second that (I am a native of that former metropolis) but I've come to realize that this view may be parochial. 1920's gangster culture of New York and Chicago has been the stuff of many movies, but only one stop for many expressions on their long journey through current speech. And who knows — some of this may be scriptwriters' ideas of what gangster speech should have sounded like.

Source: https://www.reddit.com/r/grammar/s/GioCG9RTEK

Beats me. Simply made two observations as a benefit of my recent experience:

(1) That some expressions that I too took as tough guy talk from old NY — not saying they weren't — I realized were more widely distributed, and that any particular set of tough guys were perhaps only one stop on a long dialectal journey

(2) That writers sometimes make up dialog the way they _think_ something should have sounded, or that their readers will be satisfied with, which may not be accurate. Never spoke with a 1920's gangster myself.

Source: https://www.reddit.com/r/grammar/s/kDVJFVgjvJ[/COLOR]

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1. Does the blue part mean "until"?
2. What does the red part mean?
3. Are the bold parts a long noun phrase? I'm not sure about the grammatical construction of them.

1. Up to and including
2. Based on
3. Just the first one

How can "as a benefit of" be interpreted to mean "based on"? I can't understand this.

Nothing means anything all by itself. It's only within context (for example, as part of a sentence) that anything means anything. I don't understand why people don't get that, but they don't. However, maybe it's my explanation that's the problem. Maybe I'm doing it wrong. I don't know.

A benefit of his recent experience is that he can now make two observations.

He really meant he was a beneficiary of his recent experience.

(1) That some expressions that I too took as tough guy talk from old NY — not saying they weren't — I realized were more widely distributed, ......

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The bold part is not in the usual word order.
Is "which" implied before "I realized"?

Without the parenthetical expression it's a sentence in itself.

Would the normal word order be "I realized some expressions that I too took as tough guy talk from old NY were more widely distributed"?

He's saying that expressions he thought were limited to New York were also used elsewhere. As for what's "normal" I can't say. I know I would prefer a sentence that would cause less confusion.

I would not expect to encounter that sort of thing in speech. Only in writing. (People do sometimes interrupt themselves though.)

Hopefully, the rest of the book will not cause so many problems.