I have had Progressive for years and have never had any trouble. My car got plowed into by a deer, and Progressive was reasonable to deal with. Their rates are also about the best I can find. We bundle in our home insurance (through some licensed third party) and save even more! Our rates just actually went down this past 6-month period which was a pleasant surprise.
Car insurance rates vary greatly depending on age. Your risk profile as a driver will change throughout your life, so you may be eligible for discounts at some points in your life while other times you may see your car insurance premium increase. This is why you want to keep shopping for car insurance throughout your life so you ensure the best value.
I was with Liberty Mutual for about 15 years and was very satisfied with their prices and service, although I never filed a claim. When I retired and moved from California to Florida, my auto rate went up a ridiculous amount, to almost $10,000 a year even though I had no accidents and one minor moving violation in the last ten years. On top of that, Liberty Mutual screwed up my umbrella policy and told me it was “unenforceable,” whatever that means, but I had to pay for the policy anyway up to the time I canceled and switched to Progressive, which cost about one third the cost of Liberty Mutual for an identical policy. Even good companies change over time.