What receipts do I actually need to keep?
IRS guidance generally expects receipts for purchases over $75, though keeping every receipt is safer if you have the space to store them. Digital copies count.
When are 1099-NEC forms due to contractors?
Generally January 31st for the prior tax year — file early enough that you have proof of mailing or delivery before the deadline.
What if I'm missing some of these documents?
Gather what you can and flag the gaps to your accountant early — most missing documents (like a duplicate 1099) can be requested again, but it takes time, so don't wait until the deadline to find out something is missing.
Is this checklist different in Canada?
Yes — see the Canada version of this checklist, which covers T4/T4A slips and CRA instalment payments instead of 1099s and quarterly estimated taxes.