Contract work
should be fine. I frankly blame the American government for tying healthcare to not just
employment status but
particular employer so tightly for so long. It is frankly ridiculous and disgraceful that our political leaders are not held to account for this.
The early Tea Party was supposed to be organized around a theme of "stop the nonsense and denial!" with respect to these kinds of problems, but it was quickly corrupted by the ignorant and by the people who were hoping to find ignorance. Rather than turning energy and community action into positive change, they were derided and stymied.
So now we have Trump who is basically nonsense and denial personified.
Not that Obamacare did anything to get us off the employer healthcare crutch. In that respect, things seem to have just gotten worse.
And I'm a person that doesn't think everything needs to be political! It's just hard to get around the fact that American is grossly misgoverned here. But the American voter can't bring itself to vote on real issues instead of rooting for its political team. This gives me little hope that we'll ever get the 2/3 to 3/4 consensus we'll need to practically fix this (1).
(1) Even if we don't need that many people agreeing to pass legislation, I think things like reforming entire sectors of the economy and employer/employee relationships requires very broad support to be both fair and lasting. Having 51% of voters pee in the cornflakes of the other 49% doesn't get us anywhere. Hopefully that's clear given American politics since 2006 or so.
EDIT: To tie this back to contract work, contract work is great and provides needed dynamism and small-business know-how to the economy. But it's very risky. One needs an independent source of income (other investments, working professional spouse) or a big pile of capital so you can weather ups and downs, take health sabbaticals if needed, hire temp help sporadically, etc.