Here are a couple of considerations to help with that:
1. The higher your deductible, the lower your premium -Why is that? Because when you are willing to pay more if you have a claim, the insurance company is taking on less risk. It's that simple! But is a higher deductible worth the savings? For example, if you switch one vehicle from a $250 deductible to a $500 deductible on your auto policy, the savings may only be $90/year. So, it would take you three years with no claims before that decision pays for itself. But that's just on one vehicle, if you have three vehicles and your premium decreases by $270/year, then you only need to go without a claim for one year before that decision pays off!
2. Establish a "deductible" savings account - With the above information in mind, choose a deductible for your cars and your house that you are comfortable with, then just set that money aside in a savings account and forget about it! So if the time comes when you are in an auto accident or the wind blows your roof off, meeting your deductible is one less thing you have to worry about, because the money is already set aside.
It basically boils down to what you can financially and emotionally handle when you have a claim. If you are living month-to-mouth, then a lower deductible is most likely better for you. If you are good at setting aside money for unexpected expenses, then you may be better off with a higher deductible and a lower premium. As I said in the beginning, there isn't a cookie-cutter approach to selecting a deductible. Just do what you feel is right for you!