From the article, it's not clear that the prevailing reasonable meaning was Connected Parties. In fact, it sounds like the author thought the meaning was connected parties -- otherwise he would not have bothered to disclose the relationships of the two shareholders who were connected parties (lowercase) but not Connected Parties (uppercase).
Capitalization matters very little in legalese, but punctuation is king.
This is because, unlike with punctuation, capitalization was not (and still is not) consistent across legal documents. Some people/firms use all caps for defined terms; others standard capitalization, and many don't capitalize at all on the grounds that a a defined term is not a proper noun unless it is a person, place, or thing.
In the article, the author lost half a million over capitalization. Using just that example (because it’s what we’re talking about) explain how it matters very little.
No, the author did not lose any money over capitalization. The author did not understand that capitalization was irrelevant.
What was relevant was that the author failed to properly disclosed a "connected person" as defined in the legal agreement. The law he was referencing would have done nothing to address/correct his failure, regardless of the capitalization used.
Your quote is also: "Capitalization matters a tremendous amount". But at least in some positions capitalization is mandated by grammar rules. So, when a noun should appear in such a position (e.g., just after a full stop), how does one distinguish between its two forms (capitalized and not capitalized)? There should be a way, if that "matters a tremendous amount".
