When searching how do I screen out the ones that are nightmares to deal with when a claim happens or have loopholes I wasn't smart enough to notice?
Interesting question.
My answer is the opposite of I.P., above. I'll take the cheapest there is.
Here's why: I only insure when forced to (i.e. car insurance) - otherwise I self insure. Soon I will self insure on the car as well. The odds of an accident are so small that I likely will never deal with their customer service. So I'll take the guaranteed savings over the (tiny) possibility of dealing with some hassle on making a claim.
I'd like to clarify and counter.
You'll note I specifically said, "if you're in a position of paying for insurance, you don't necessarily want to cheap out." It may have been slightly poor phrasing, but the implication in that statement was that if you're in a position of
having to pay for insurance coverage whether you want it or not, you shouldn't cheap out.
With any and all insurance where the coverage is for you and your property directly, if you have the liquidity to be able to eat most potential claims on your own, absolutely... cheapest insurance to none with terrible customer service is ideal as the money you could save can and frequently does outweigh the actual money spent.
However, the instant we switch gears into insurance coverage that covers you and any liability on damage that you may incur to others? Forgive me for saying this, because I do try and be respectful and keep my cool, but if you specifically lowball and get the cheapest minimum coverage auto insurance available and God forbid you get in a wreck and it's
your fault? We're all humans, we all make mistakes. But anyone who makes another person suffer due to their negligence
and their deliberately cheap insurance coverage? Get stuffed. The thing is, if you got the assets to step up and make right what your insurance company won't cover in this sort of scenario, good on you... but again, we're all humans, and quite frequently when money and potential criminal charges are on the line, almost
nobody steps up and takes the responsibility they should. Saying you will and having that statement untried in your life is disingenuous. I know we'd all like to say we're noble and honest... but this is the sort of thing you can never be certain about your character on until the rubber hits the road.
I've lived the consequences first hand of being hit by a cutrate insurance policy holder for the past 17 years of my life. I can assure you I would have literally been better off long term if the driver was simply uninsured (for as much as having zero insurance coverage is worth - it's still one of Dante's Circles of Hell). I learned a valuable lesson three months after that Valentine's Day: Use an insurance company that will make good on claims, and carry a quarter-to-half-million dollar policy plus medical on yourself and for uninsured.
I'd also like to point out that it's been uninsured motorists in the state we live in that forces our vehicle insurance to be some of the highest in the country. We wouldn't be paying $1300/year for two old beater vehicles if not for the long standing history of allowing people to "self insure".
Frugality is valuable and important to all of us, but don't be stingy when it involves your potentially destructive actions and other people. Your decisions with vehicle insurance impacts more than just
your bottom line.