On the payroll tax memorandum, @JimRoyalPhD does a great job of breaking down the obvious caveat: It's a deferral, not a cut.

Experts are debating whether the holiday (from Sept. 1-Dec. 31 for those making up to ~$104,000) will actually move the needle. https://www.bankrate.com/taxes/trump-payroll-tax-deferral-executive-order/
Trump's student loan memorandum is likely the easiest to implement (and will steer clear of other barriers), simply because it extends federal borrowers' forbearance program already in place by three months, moving the Sept. 30 expiration to Dec. 31. https://www.bankrate.com/loans/student-loans/trump-executive-orders-student-loan-relief/
The $400 unemployment boost is without a doubt the wonkiest & most contested of the four orders.

UI experts and lawmakers are expressing concerns re: constitutionality & implementation, meaning big roadblocks before Americans get $$$. https://www.bankrate.com/banking/federal-reserve/how-trump-400-unemployment-boost-works/
More:

- Eligibility: Individuals who receive more than $100 in weekly UI checks (meaning more scaled than FPUC)
- Should last until Dec. 6, or until funds run out, whichever comes first
And a preview of a few barriers:

- Funds will likely only last 5-6 weeks
- States will find it hard to fund their share (which might be required to receive feds' portion)
- States' regular UI payments *might* count toward match, but what does that mean for federal-funded PUA?
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