Kathleen DeLaney Thomas (North Carolina; Google Scholar), Improving the Tax System for Independent Contractors: Quarterly 1099s, 182 Tax Notes 79 (Jan. 1, 2024):

In this article, Thomas proposes a new quarterly form sent to independent contractors that would inform them of their quarterly earnings and their obligation to remit estimated taxes on that income, easing the compliance burden on those taxpayers and helping decrease the tax gap.

Conclusion
Imagine a young taxpayer decides to drive for Uber at night to supplement her income. On top of a modest salary she earns at her day job, imagine this taxpayer earns $20,000 driving for Uber in her first year ($5,000 in each quarter). If she has never earned self-employment income before, it might not occur to her that she owes estimated taxes during the year. When she files her tax return the following year, she might be unprepared to learn that she owes significant tax on her Uber earnings and has incurred an estimated tax penalty. And if she has not properly budgeted, she may not be able to afford what she owes the IRS. The current tax system ensures the IRS will find out about the Uber earnings, because Uber will issue a Form 1099-K. But the law does very little to help this taxpayer succeed in fulfilling her tax payment obligations.

Consider, instead, a scenario in which this hypothetical taxpayer receives a Form 1099-ES from Uber each quarter. That Form 1099-ES informs her she has earned $5,000 for the quarter and that she is responsible for paying taxes on her earnings, and it gives her instructions stating that she may calculate her quarterly estimated tax payment as 5 percent of $5,000 (or $250). By the time the taxpayer files her tax return, she will have paid $1,000 in estimated taxes, potentially avoiding any balance due with her tax return and avoiding penalties.

Both taxpayers and the government would benefit from quarterly Forms 1099. What’s more, requiring third parties (such as Uber) to send quarterly tax forms to independent contractors would impose tax compliance costs on those entities that are best suited to handle those costs efficiently. This reform would not only bolster tax collection but also bring much needed tax simplification to independent contractors who struggle to meet their tax compliance obligations.