Sentence 1: What does that say about your political judgment?

Sentence 2: What does you not paying taxes say about your judgement?
Is this second sentence entailed by the first?

Answer: it is not possible to tell

Sentence 1: Many Gothic and Renaissance buildings have been lovingly restored.

Sentence 2: Many of the ancient buildings have been restored.
Is this second sentence entailed by the first?

Answer: yes

Sentence 1: The funds are part of about $2.

Sentence 2: The funds add up to $2.
Is this second sentence entailed by the first?

Answer:
yes