re: HSA vs Traditional Health Insurance

Taking the dental part out of it (as dental is not health insurance), what's the premium difference between the two plans? That difference automatically goes into the HSA. Then, can you make up the additional amount needed to fully fund your HSA?

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My only concern is my wife and I are looking to have a baby within the next year or so,

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Be careful with this. The math makes a lot of sense for young healthy people with no kids. Getting a pregnant makes your wife "unhealthy" - in that she will have increased medical expenses - and kids always have medical expenses.

Just look very closely at what the high deductible is, and what the cost sharing is after the deductible, compared to the traditional plan.