Owning insurance is one of the most important things you'll ever do for yourself and your family. The problem is, there are so many different kinds of insurance for so many different things. There's health insurance to cover medical problems, there's car insurance, there is life-insurance, there's home insurance in case your house burns down... the list goes on and on and on.
In America we live in a society based on risk. That's what freedom means... risk. The government leaves us alone to make our own choices, for the most part, and that is what our capitalist system is built on.
The problem is, when people make their own decisions they very often make the wrong ones. This can have catastrophic effects on every aspect of our lives. The way our system has evolved to cope with these problems is through insurance.
It's a happy middle ground... the government leaves us alone to make her own choices, which means they leave us alone to make stupid choices, but then we can mediate some of the stupider choices by buying insurance to cover us in case something goes wrong. Everybody is happy... freedom is maintained, but our stupidity that's inherent in every human person, doesn't run wild.
So to say "I'm not going to buy insurance" is probably not the best mindset to have, you can be sure! The government actually mandates that you legally are required to own certain types of insurance such as car insurance. If you borrow money to buy a home, the bank will require that you have homeowners insurance to cover their loss in case the house burns down. And I don't think anybody needs to be convinced of the importance of health insurance.
All of this leads up to the main problem... which is, how to pick the best insurance company. With so many insurance options you have got to pick the right insurance company who will honestly work with you to give you just the coverage that you need and nothing more. If you let certain insurance agents walk all over you, they'll sell you everything under the sun. Before you know it you'll be insuring your dog against the flu!
The first rule of thumb is to pick a major insurance company that has the financial resources available to backstop their insurance claims. Many people purchased insurance from AIG over the last few years thinking that their claims would be paid. But when the financial crisis of 2008 hit and AIG for all intents and purposes went under; those insurance policies were no longer guaranteed. Luckily the government stepped in, but you can't always be sure that will happen.
Next pick an agent that you are comfortable with, make sure they understand your financial situation and your insurance needs and make sure that they know that you will not tolerate being hard sold additional insurance that you don't need.
Finally ask around... ask the people around you who they turn to for insurance help. In no time at all you'll probably find a consensus on who the best people in your area are. Many times personal references go a long way in the insurance industry.