I understand what you're saying, I may edit that a bit, for it wasn't my intention to make the reader think that Tolkien didn't like Boromir that much. Although, I do think that the "bossy brother" quote is in a negative light. As Tolkien obviously prefered Faramir much more, some of the qualities Boromir didn't have are present in Faramir, and as Tolkien was talking about Faramir in Letter #244:
"He was motherless and sisterless...and had a 'bossy' brother. He had been accustomed to giving way and not giving his own opinions air..."
Tolkien goes on to praise Faramir even more. So in that respect, I see the "bossy brother" comment as a definite negative on Boromir.
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