Sentence 1: But representing this group, a group that often lacks education and legal sophistication, can challenge even the most-dedicated attorney.

Sentence 2: It is not a challenge for attorneys to represent them.
Is this second sentence entailed by the first?

Answer: no

Sentence 1: Instead of writing this book--and book-writing is surely a job for sissies--he should have gone out and beat someone up or sold drugs.

Sentence 2: He ought to have been in school studying hard.
Is this second sentence entailed by the first?

Answer: no

Sentence 1: and uh you know the batteries carry it for at least four or five hours

Sentence 2: The batteries should last for around 4 hours or so.
Is this second sentence entailed by the first?

Answer:
yes