Does your country or province have a way to shop for health insurance for people who are self-employed or unemployed? For example, in the US even before the ACA law went into effect, you could still shop the websites of health insurance companies individually and get quotes. Now that the ACA is law, you can even more easily just get ballpark quotes from healthcare.gov or ehealthinsurance.com. So for me, I got quotes for myself at fictional ages of 50, 55, and 60 years old in order to project what my health insurance will likely cost in present day dollars.
By age 65 everything switches over to Medicare & supplemental coverage, so basically I only have to cover the time period from when I leave the workforce around 46-50 years old until age 65. Is there something similar for where you are? I agree that healthcare costs are something it's very important to have insured. You could have years of being totally healthy, then get hit with a $120k hospital stay. It would be nice to have that capped at an $8000/year out of pocket maximum with insurance, for example.