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My answer is (D). It took me 02:04. I spent quite some time checking (D) against (A).

To start with, I could not really understand what (A) means. "as broad as to fail to" is so clumsy. Yet, we cannot eliminate an answer simply because it is not to our taste.

But, I do need to understand the meaning of the sentence! When I get stuck at one option, I sometimes reverse the order of options.

(E) "so broad that he fails..." makes the meaning much clearer.
But (E) is out because we need to use "fail to do something" rather than "fail in doing something".
Actually, "fail in doing something" is not 100% wrong. It means "in doing something, someone fails".

(D) Seems ok. Keep for now.

(C) Need to use "distinguish X from Y". Eliminated

(B) "Fail to" instead of "Fail in". Eliminated.

(A) Still does not like (A) but tries to find another issue to eliminate it.
In "distinguish X from Y", X and Y should be parallel. Here, "the sale" (a noun) and "collecting profits" (a gerund) are not in perfect parallelism. In (D), "selling" and "collecting" are parallel.
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The income categories of Senator Crocker’s proposed tax code are as broad as to fail to distinguish the sale of an old chair at a pawnshop from collecting profits in a sophisticated stock option move.

A) as broad as to fail to distinguish the sale of an old chair at a pawnshop from collecting profits in Incorrect

the sale of an old chair and collecting profits are not in parallel

B) as broad as to fail in distinguishing between the sale of an old chair at a pawnshop and collecting profits from Incorrect

fail to - correct idioms,
the sale of an old chair and collecting profits are not in parallel

C) so broad as to fail to distinguish selling an old chair at a pawnshop and collecting profits from Incorrect

......distinguish....from..., not distinguish....and .....

D) so broad as to fail to distinguish selling an old chair at a pawnshop from collecting profits in Correct

E) so broad that he fails in distinguishing between selling chair at a pawnshop from the profits in Incorrect

between a and b, not between a from b
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