The first thing to do is estimate your past usage (roughly). So you had 1 doctor visit, wife had 2, kids had 4, whatever. And look at about what each costed, in total, using the "allowed" cost (not the fictional price, but instead what the secret price between the provider and the insurance company was). Also, not what you saw on your credit card, since that could have been reduced with copay/co-insurance. Add in any prescription costs. Again, the cost not to you, but the total cost that was paid to the provider. Use these totals to get what your expected next year medical spend will be. Obviously it's just a guess, but it's the best you can do.
Now, when you shop for insurance, you add the grand total of the premiums (12 times your monthly payment to the insurance company) plus whatever the estimate, from above. So this is your expected outlay for premiums plus medical goods and services, priced using the advantageous pricing the insurance company has negotiated, but without your insurance "kicking in".
Now, for each policy you're evaluating, apply the rules of the policy to see how much they will kick-in. For instance, if you get a high deductible policy, and you don't have too much utilization of medical goods and services, then the total they kick-in will be zero. But if you evaluate a super-duper policy where you see the doctor for $50 max, and a specialist for $75 or something like that, subtract from the total whatever those kickbacks will be.
So if you pick a cheap, high deductible policy, the premiums would be cheaper, but you'd get no kickbacks for services. These policies work, financially, for people who don't have routine medical stuff. If you pay big bucks in premiums for a policy that gives you more kickbacks for when you utilize medical services, and then don't use medical services after all, you end up paying for stuff you don't use.
So that's the gist of it, from my perspective, but there's one more thing to consider. If you're on the fence between a high deductible policy, you DO get a tax break for having a high deductible policy; you're able to lower your income (not pay tax on it) by a certain amount (on the order of $7000), so if you're in the 28% bracket, that can be worth a couple of grand.
Good luck in your shopping. They don't make it easy.