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雖然這幾句從語意看得出來，但你問的是為什麼不能這樣用、那樣用，所以用文法的詞類或屬性來說明：

[1.One protestor held a sign that read "People need jobs"
為什麼that不能用with代替?]
注意 that 後面是動詞過去式 read， with 是介係詞，不能直接接動詞。 關係代名詞 that 才能當主詞，接動詞。

[2.The board of directors is at a loss to find a better company policy whose application will benefit mgt and union alike.
為什麼whose不能用that 或its代替?]
that 當關係代名詞只能當主詞或受詞， 這裡關代後的子句， application 是主詞， mgt and union 是受詞，所以 that 不能用。 而 its 是所有格，卻沒有連接詞功能，只能用 whose，是關代的所有格，同時具有所有格和連接的功能。

[3.With their annual budget reduced to one-third that of the previous year, this upstart company had trouble paying the salary of it's regular staff
請問為什麼that不能用as代替?]
that 是代名詞，取代 annual budget，可以有介係詞片語 of the previous year 來修飾。 而 as 是介係詞或連接詞，要接名詞或子句，所以不能用。

[4.That a more flexible schedule is nowhere in sight saddens every employee's heart.
為什麼that不能用because代替?]
because 是從屬連接詞，一定有兩個獨立的子句，各有主詞動詞。 這裡如果用 because，那前一子句主詞是 schedule，動詞是 is，後面動詞 saddens 就沒有主詞了。

這句 that a more flexible schedule is nowhere in sight 是主詞，saddens 是動詞。 文法稱 that 引導名詞子句當主詞。

[5.Unbelieveable as the rumor of insider trading may seem, an investigation into it by the board has begun
為什麼as不能用in代替?]
這句有逗點，前面是一個子句，後面也是一個子句，必須有連接詞才行。  as 是從屬連接詞沒問題。 in 是介係詞，不能連接子句，所以不行。

[6.While the parts are being assembled, the mechanics should be brought up to date about the latest engine
為什麼about不能用with或of代替?]
這是搭配字問題。

慣用語 「bring 某人 up to date」 是 「讓某人知道最新狀況」。 這裡是被動 be brought up to date。

至於知道什麼東西的最新狀況，用介係詞來表示 「關於」，about 搭配絕對正確，英美也有很多地區的人用 with 或用 on，所以 with 也可以，但 of 不行。 of 通常是和 inform、 accuse 搭配。

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