You're conflating small companies with a few employees and revenues in the thousands to millions with massive quasi-governmental institutions with profits in the billions. The first group doesn't have access to inexpensive healthcare (because their risk pools are small and they don't have much negotiating power), they don't have access to lobbyists to write laws for them, and they don't have access to armies of lawyers that can twist the meaning of laws already on the books.

The "free speech" issue really only applies to companies that have the resources to influence the government to begin with. A startup that has five employees and is only ramen profitable isn't going to hire a lobbyist.

On the other hand, I do think you're sort of right. If a benefit like this were passed, a lot of unemployed people would suddenly become "entrepreneurs" to get free healthcare. Large companies would find ways to spin off into thousands of "new" shell companies and transfer their employees there to get free healthcare as well.

Of course, the way the healthcare system exists now is basically that the government subsidizes entrenched players with tax incentives and allows employment to become essentially indentured servitude because the risk of losing healthcare while switching jobs is just way too high.