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Lets start with meaning analysis.
Here the meaning can be inferred easily.
Councilman proposes a plan to beautify the city and attract tourists.
His opponents oppose the plan by stating that it wont attract tourists and is overly expensive.
Also , the plan has been compared to putting lipstick on bulldog ie putting lipstick on bulldog wont beautify the bulldog similarly the councilman proposal of city dump wont beautify the city.

Error Analysis
which refers to the closest noun. Hence here which refers to TOURISTS. This reference is incorrect.
The intended meaning is .. opponents compare the proposal of councilman to putting lipstick to bulldog.

Answer Choice Analysis
A. INCORRECT.
B. INCORRECT. ( Same reason - WHICH)
C. INCORRECT.
Not unlike putting lipstick to bulldog is grammatically incorrect and the sentence structure is inappropriate
D. CORRECT.
Comparing is the verb-ing modifier , modifying the previous phrase. (His opponents......)
Here IT refers to the PLAN
E. INCORRECT.
This is grammatically correct but meaning wise incorrect.
Intended meaning is putting lipstick on bulldog.
Not the bulldog already wearing the lipstick.

Thanks.
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Priyam has done a fair analysis, so I will not rewrite the same thing.

But, I have a few thoughts on why (D) is better than (E) here.

If you look at the sentence, the comparison is between two actions, not nouns. The first action is beautifying the city by landscaping dumps, so the compared entity with this plan (which denotes an action) should be another "action" - "Putting lipstick on a Bulldog", shown by the usage of a Gerund (which depicts an action) in option (D). In (E), however, the plan's comparison is made with a bulldog. This is incorrect.

This is why (D) triumphs over (E).
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PyjamaScientist
Priyam has done a fair analysis, so I will not rewrite the same thing.

But, I have a few thoughts on why (D) is better than (E) here.

If you look at the sentence, the comparison is between two actions, not nouns. The first action is beautifying the city by landscaping dumps, so the compared entity with this plan (which denotes an action) should be another "action" - "Putting lipstick on a Bulldog", shown by the usage of a Gerund (which depicts an action) in option (D). In (E), however, the plan's comparison is made with a bulldog. This is incorrect.

This is why (D) triumphs over (E).

Hi, but I think “it” is a pronoun, only can stand for noun but cannot stand for an action. So confused...
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Mavisdu1017
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Priyam has done a fair analysis, so I will not rewrite the same thing.

But, I have a few thoughts on why (D) is better than (E) here.

If you look at the sentence, the comparison is between two actions, not nouns. The first action is beautifying the city by landscaping dumps, so the compared entity with this plan (which denotes an action) should be another "action" - "Putting lipstick on a Bulldog", shown by the usage of a Gerund (which depicts an action) in option (D). In (E), however, the plan's comparison is made with a bulldog. This is incorrect.

This is why (D) triumphs over (E).

Hi, but I think “it” is a pronoun, only can stand for noun but cannot stand for an action. So confused...
Hi Mavisdu1017,
"It" here is not acting as a pronoun but rather as a "placeholder". You can read more about "placeholder it" here
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Mavisdu1017
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Priyam has done a fair analysis, so I will not rewrite the same thing.

But, I have a few thoughts on why (D) is better than (E) here.

If you look at the sentence, the comparison is between two actions, not nouns. The first action is beautifying the city by landscaping dumps, so the compared entity with this plan (which denotes an action) should be another "action" - "Putting lipstick on a Bulldog", shown by the usage of a Gerund (which depicts an action) in option (D). In (E), however, the plan's comparison is made with a bulldog. This is incorrect.

This is why (D) triumphs over (E).

Hi, but I think “it” is a pronoun, only can stand for noun but cannot stand for an action. So confused...
Hi Mavisdu1017,
"It" here is not acting as a pronoun but rather as a "placeholder". You can read more about "placeholder it" here
Well understand. Much thanks PyjamaScientist
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