How much should I pay in auto insurance?
Yes, they can and do check.
I only know this because when I was applying to NJM they saw that there had been a claim on my car. At first I was confused because I hadn't filed any claims, and then I remembered that my mechanic had been involved in an accident while test driving my car after doing a repair. Since neither my husband nor I were driving, and the claim was not on our insurance (our mechanic's insurance paid the claim) it wasn't held against us.
I only know this because when I was applying to NJM they saw that there had been a claim on my car. At first I was confused because I hadn't filed any claims, and then I remembered that my mechanic had been involved in an accident while test driving my car after doing a repair. Since neither my husband nor I were driving, and the claim was not on our insurance (our mechanic's insurance paid the claim) it wasn't held against us.
Insurance companies ding you for 3 years (it actually can be longer than, depending on when it shows up) after a claim, accident, ticket, etc. You pay a premium. Also, most only offer their top tier rates to clients who have a clean record for 5 years, hence the question.
UPDATE: I got about 2200 per year cut from our insurance. I can't believe I was paying so much. I was confused by the "six month" premium, which actually was twice yearly. So stupid. Maybe in the future I'll change insurers more often so I don't fall asleep at the wheel 
without knowing your driving histories it is impossible to say how much is reasonable...but with brand new $25k car, a driver with a good record can get insurance for about $100-150/month. I would guess 2 good drivers with 2 cars would be about $200-250/month.
Also a function of how much coverage you want and your particular driving experience
Also a function of how much coverage you want and your particular driving experience
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shanabana