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Well, in my opinion, it's not worth getting his insurance. i paid 6k bells for it and I've only earned back 2k bells in the 1 year I've played it. But if you want to pass it, here are the answers i can remember:

I have been the victim of frauds and scams. True

I have a plan for the inevitable future. False

I haven't played the game for a while but I'm pretty sure he asks you 3 questions, but he has 6 questions so you should get a different set every time.

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12y ago
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Q: How do you pass Lyle Quiz on animal crossing wild world?
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