No. of Recommendations: 3
Depending on the monthly health insurance premium and the number of loopholes in the policy that could still cause bankruptcy if he gets sick, I could see holding off on the health insurance until I had more financial assets to protect.

Speaking from a bit of experience, health insurance can also determine both choice of treatment and speed of access to that treatment. It may also show that you are insurable in the future. At that age, health insurance with about a $2500 annual deductible is under $200/month.
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