Sentence 1: He expressed concern about how to reflect this complexity in the recommendations.

Sentence 2: He was concerned about how he should indicate the complicated recommendations.
Is this second sentence entailed by the first?

Answer: yes

Sentence 1: uh-huh uh-huh that would be wonderful to be able to play and of course from our town a lot of people go to Arizona or Florida for the winter and they're able to play all year round but

Sentence 2: A lot of people from our town winter in Florida or Arizona.
Is this second sentence entailed by the first?

Answer: yes

Sentence 1: This was also to be the starting point of the Third Crusade in 1190, when England's Richard the Lion-Hearted joined forces with Philippe Auguste.

Sentence 2: The Third Crusade started in 1991.
Is this second sentence entailed by the first?

Answer:
no