>As an employer, W2 forms aren't terrible hard to fill out You're taking my example too literally. The "W2 filing" is shorthand for all the extra legal complications such as withholding taxes, paying employer's portion of Social Security, Medicare, and any state mandated payments such as worker's comp, etc. All of that is a big leap of complexity compared to just pushing a few buttons on an iPhone and getting a service-on-demand.
>And then of course, no one would pay a babysitter a W2. You'd count them as a 1099,
Unless the IRS (or even the babysitter) wants to reclassify the relationship as W2 instead of 1099.[1] Now the consumer owes back taxes (and possibly penalties) which is more complicated (and more expensive) than using a phone app.
>What's more interesting is having an actual employee
Sure but probably 95%+ of consumers who want to periodically use Instacart / Uber / Blue Apron / etc do not want jump to the next level of complexity with an actual employer+employee relationship. The threshold for inflicting that bureaucracy on oneself is high. Lastly, the extra employee taxes a consumer would have to pay makes the W2 relationship more expensive than a naive calculation would suggest.
[1] https://www.nytimes.com/2015/03/14/your-money/contract-worke...