1) yes 2) you are assuming that it was even possible to buy health insurance as a single person prior to the ACA. I actually tried and found it incredibly difficult.

So what realistic options did self-employed have before the ACA: either pay for an expensive insurance or be uninsured? What did most typically choose?

(Obivously the IAMAE note applies here)I choose uninsured because I was young...and dumb. There were some options out there, especially for add on things like dental and vision. Insurance was available, but it was hard to find as an individual and very expensive in my experience. COBRA was an option but was still tied to a previous job and had limits.

As an entrepreneurship scholar, I see health insurance as one really strong limiter of entrepreneurial activity in the US. The lack of single payer significantly privileges those with the means, the young, and those without children to conduct entrepreneurial activity.

Yes, at least the tech employers that most of us are likely to work for. And, with the repeal of the ACA imminent, this seems relevant: employer plans usually didn't discriminate on pre existing conditions. Individual plans did.

Would you be able to quantify the difference somehow? Individual plans where more expensive by a factor of two, or more?