Obamacare created new gaps that absolutely sucked - made over 58k and self employed? No subsidies for you and paying a skyrocketing premium higher than any reasonable home mortgage with a 10k deductible. Completely unrealistic. And then the IRS hit you for thousands in penalties via the individual mandate.
I lived through that, uninsured, for five years or so as a business owner - to “rich” to get subsidies, too poor to afford 20k+ per year for nothing except a theoretical out-of-pocket max (I say theoretical because there are many exceptions, loopholes, and the annual reset). Being hammered by the IRS for this was.. just.. swell.
So for me Obamacare sucked because it made the cost of individual market plans completely unaffordable and then taxed me for not being able to afford it. As a business owner responsible for employing others, it seemed especially ridiculous because here was a strong disincentive for me to continue on, which would mean a negative ripple effect beyond just me, i.e. layoffs, if I shuttered the operation.
Once the individual mandate went away, and some new options for employer cost sharing like QSEHRA/ICHRA came about, it has gotten a bit more manageable, but most small business owners I know still struggle with healthcare. Cost sharing programs like CHM are about the only workable alternative but they don’t offer the kind of bankruptcy protection a solid insurance premium would cover, and they are religious by nature. Alternatively, DNR and a term life insurance policy.
Best option is to be married, have spouse work for the man to get into corporate group plan for family, while you grow your business enough to sustain an insurance scheme.
But it sucks out there on the individual market - the raw actuarial numbers to insure you are bad - and subsidies disappear quickly with any amount of AGI. Since the vast majority of Americans are on employer-paid healthcare plans, this is a view into it that most don’t see. The cynical side of me (as a small business owner) says this is by design to keep you working for corporate America - consolidation of labor, consolidation of the profits. For me, Obamacare further entrenched this aspect of the system, which has become more terrible, not less.