Sentence 1: i like to rough it

Sentence 2: Besides roughening it, I'd also like to break it after.
Is this second sentence entailed by the first?

Answer: it is not possible to tell

Sentence 1: If so, it explains the steps in a final assessment and the actions to take, depending on the results of your additional work.

Sentence 2: There is no real way of explaining the steps or actions to take, it's pretty confusing anyways.
Is this second sentence entailed by the first?

Answer: no

Sentence 1: It was a pretty black night, and the carriage drive up to the house was dark as pitch.

Sentence 2: It was sunny and clear as the carriage drove to the house
Is this second sentence entailed by the first?

Answer:
no