You do now. Before my wife was able to reach age for Medicare, she was paying $1,180 per month, or over $14,000 per year for health insurance. That was with a $2,500 deductible, and did not cover another $2,000 of medications she needed. This was without any major medical issues.
Her last year working as a Dental Hygienist, she earned about $28,000, resulting in $23,000 after taxes. Dental workers for the most part do not get employer supplied health insurance. The only given is that the Dentist usually will provide dental care to each employee. When we did the math, after health costs she had $5,000 total. I feel for this family, as I personally have seen too many cases of financial ruin due to medical expenses.