HSA vs Traditional Health Insurance

You do realize that with a Health Savings Account, you would have to switch to a high deductible plan?

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Yes I understand this, but if I'm paying out $5,200/year for insurance and out of pocket cost would not equate to this then wouldnt it be financially beneficial to pay the out of pocket expense up to high deductible and also have the extra money in the HSA?

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Yes. I just made the switch this year. Same age as you and don't go to the doc a lot. For me, the HSA plan premiums are 40% of what the traditional plan premiums were. Now I am taking the 60% leftover and throwing it in the HSA which rolls over each year.

If I have a major accident or something unforeseen happen where thousands of dollars in medical costs pile up, then it won't be worth it. It's a risk I'm willing to take at this point in my life.

How much does the HDHP cost you vs the plan you have now?

You seem to be leaving that out

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.