Health Insurance for Self Employed (Sole Proprietorship)

Likely nobody will offer you a group benefits plan, even through an industry association. Don't waste your time.

You should look into two options:

1. A pared-down personal benefits plan. It's not going to be as good as a corporate group plan, because those rely on sharing the burden with a substantial portion of employees who pay for benefits but make little use of them.

2. A corporate Private Health Services Plan (PHSP), for example: https://www.brockhealth.ca/. The PHSP is basically pay-your-own-way. It allows the same type of claims as a group health plan. You will pay for everything, but the advantage is that it is a business expense to the company with no deductible, and therefore tax-free. If you paid for it personally, it would be subject to a large medical expenses deductible on your taxes, and therefore not tax-free. The CRA requires that you follow the rules for a PHSP regarding what is claimed and how it is documented, and they often scrutinize the first-year claims for a sole proprietorship very closely, so it helps to have an expert company manage the claims professionally in return for a small commission (5%).

You may wish to check out the offerings from sbis.ca for coverage (if not cost) similar to a typical group benefits plan. I have used them in the past when I was a sole proprietor with coverage provided through Green Shield.

I also agree with the PHSP suggestion if it suits your circumstances. This is a current area of research for me and I do not yet have any direct experiences with this type of plan.