How do you keep up to date with insurance coverage?

The best thing is to keep it simple. For instance, I pay my car insurance for the entire year with my tax return. If you pay monthly, make sure you have the money in your bank account the week it is due. You can have the company automatically withdraw it, write a check or obtain a money order (they don't take cash). Mostly it is just a matter of planning ahead to have the money in the bank at the right time.