If I drove for Uber/Lyft for moonlight income, I would prefer to paid purely in cash instead of being forced to be paid in health insurance, pto, etc. since all of that would be provided by my primary employer.
You aren't paid in healthcare at an hourly job. There is an employer healthcare plan you can buy into if you want. If you have insurance through your parents, spouse, another job, you just don't opt in.
At lower paying hourly jobs typically the employer doesn't cover any of the cost. For many these are prohibitively expensive, even if you work full time. Typically for higher paid work, most salary positions, the employer covers most of the cost.
My last employer did. You could only opt in/out once a year or during major life events, but it gave enough flexibility that I could have higher pay or more benefits when it suited me.
Practical barriers in terms of the maximum limit of complexity legal and HR are willing/able to take on and remain effective while dealing with? Absolutely. Everyone thinks "It shouldn't be that hard!"
In reality, it kinda is. HR abstracts away the complexities of jurisdiction specific hiring requirements from the rest of the org, and legal does much the same. If you ask for extraordinary accomodation, I'm not saying it won't work, but I can guarantee you will experience friction while HR/Legal figures it out.
On the plus side, if it works, new employment template. If it doesn't, you don't get offered the job.
I've ended up the awkward giraffe in a couple places. You being flexible, and the HR/Management recognizing your unique capability to create value helps. However, when talking Gig work, they will invariably go for the template approach. There's also the fact that Gig work really conflates the distinction between "contractor" and "employee" in the sense that contractor carries with it an assumption you are providing for your own affairs. The compensation you quote them should have parity with their total outlay for an employee to do the job, because you should be arranging the same things for yourself; thereby obviating your need for the employer to do it. The thing you get out of by the contract route is all that paperwork and process overhead. You do a one-time disbursement of funds, and donezo.
The problem is, no one ever tells you (the contractor) that, and Uber et al does not let you quote price or have input on the cost calculation. So you accept super under-bid compensation, because you don't know the difference between a market rate and a hole in the wall, or an appreciation for the total footprint of the business model.
Uber, and services like it, make their money by predating. on this ignorance. This is not to say that stuff like "licensing" gig workers to vouch for the fact they really know what they are doing is really a good idea... I'm kind of curious though what kind of effect that sort of thing would have on the worker pool. Like a short course that make sure they understand the accounting. Wonder if an experiment could be run with that sort of thing somewhere and how it would effect the market.
That being said, it kinda kills the value prop of people just needing a few bucks here and there, but I question the seductive simplicity underneath that pitch, because everytime I've run into something that's pitched that way there's a big ole ugly iceberg beneath it.
Why not go one step higher up the abstraction, which is one step better, and provide healthcare irrelevant of jobs - it doesn't matter if you have 1 or 2 or none. You still have healthcare!