Someone drives 40 hours for Uber one week, and then goes away for two months. How much health care do they get? Do they get cash or a week of benefits?

How much cash?

Same as the W2 employees but prorated?

Technically even full time W2 employees don't have to get health insurance or paid time off. So what if they company doesn't offer insurance or PTO to their employees. Are they off the hook?

Your system sounds good but unfortunately isn't tenable.

Ironically, if we had single payer healthcare that was funded by taxes, the entire thing would be moot. You'd pay into health care based on what you earned, and you'd get out the same as everyone else.