Sentence 1: Jon wondered for a moment how lucky they had been to pick the right spot for their retreat until the answer came to him.

Sentence 2: Jon wasn't sure how they'd gotten the perfect spot for their retreat.
Is this second sentence entailed by the first?

Answer: yes

Sentence 1: He is relocating to his home state of Georgia.

Sentence 2: He is going to Kentucky.
Is this second sentence entailed by the first?

Answer: no

Sentence 1: That's always struck me as strange.

Sentence 2: That seems odd to me.
Is this second sentence entailed by the first?

Answer:
yes