Like the current Uber driver case.
There are laws about what constitutes contractors vs employees - both federal and state. If you satisfy N out of M items in a checklist, you are an employee, regardless of whether both parties want you to be.
Controlling how you do your job is one of them. If the employer directs how you can do the job and doesn't give you freedom to do it your own way, that's a major item.
If your employer doesn't let you bring your own equipment, that's another one.
If you do not have a chance of losing money on the contract, that's another one. Say you hire a contractor to repair your roof, and he screws it up. Typically he is expected to fix it even if he ends up with a net loss (or he can refuse and not get paid at all). When an employee screws up, the worst that will happen is he'll get fired.
And so on.
It's very unlikely these people can be contractors unless he's hiring experienced folks who know the equipment.
I think you have misunderstood the suggestion; it's not about contractors vs. employees, it's about fixed-term versus not.
Fixed-term employees are not classed as contractors. They are regular employees with all the usual benefits and rights of employement - except that it comes to an end at a pre-determined date, unless extended.
Regulations have many unseen side effects that end up causing damage, people should think harder about them and they would realize that in many cases (most in my opinion) they do more harm than good.
Everyone's already charging more for masks, he should be able to manage a decent market rate. To begin with, unemployed people in a pinch are probably willing to accept slightly lower pay.