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It makes sense to go high deductible no matter what your income is. It costs less to pay interest and principle on your $10k disaster deductible than it does to pay $2k/year extra on low deductible health insurance.

Insurance is a tax on people who are bad at math.

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This is complicated somewhat by tax law. Your company paying for the more expensive plan is paying it out of pre-tax money, whereas your deductible (up to a point) is paid out of post-tax money (unless it comes out of an FSA, but those being "use it or lose it", one should be careful not to over-fund, so they aren't a good match for paying unexpected deductibles).

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