I think that if you open your gates he will go and sit in the roost, but I am not shore. Try it!!!
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I don't think there are any real answers. He'll make you pay for insurance no matter what.
Once a week, and you can talk to lyle on saturdays to change what time a week he comes.
You might not know this, but YOU can actually choose when Crazy Redd comes to your town. First talk to Lyle on Saturdays(I know we all hate him but it's the only way!). Lyle is the weird salesman otter that's outside your house on Saturdays. Talk to him. Fill out the questionnare. Then he will ask you what day do you want Crazy Redd to come. You decide.
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.
mostly in Lyle House