Ask HN: Remote engineer or contractor? A nuanced hiring situation

Joanne is a rockstar SW engineer in Canada, working as a contractor for several years bringing in ~$150k annually. The Boston-based startup Foobai want to hire her as one of the first few engineers. They've agreed to the following comp: $90k salary, 2% equity. The salary isn't quite enough to support herself financially, so Joanne wants to pick-up a side gig. Foobai agrees to this, as long as Joanne fulfills her responsibilities. Some questions:

1. Should Foobai hire Joanne as a contractor or an employee [1]?

2. Are health and other insurance benefits given to independent contractors?

3. How are those benefits given to international employees/contractors?

[1] https://gusto.com/blog/hiring/hire-employee-or-independent-contractor