1099s
Nobody likes 1099s. They are the most annoying thing in the world of accounting and bookkeeping, and they just get more annoying with all of the changes.
Now the 1099 NEC Box 1 is the new 1099 Misc Box 7.
My advice to you is just get them done. Get them done as quickly as possible. Spend the least amount of time possible on them. This is an extremely low value, high compliance type of service. In truth it’s a big waste of time, but you have to do it.
If you paid a contractor with a credit card you do not need to 1099 them. Hint: Pay ALL of your contractors with credit cards and enjoy the month of January a whole lot more.
Some situations are trickier than others.
PayPal issues a 1099K so if you paid via Paypal, don’t issue. Read all about it on the PayPal site --> how-does-paypal-report-my-sales-to-the-irs-will-i-receive-a-1099-tax-statement-faq729
Venmo (owned by PayPal) issues a 1099K, like PayPal, subject to thresholds, same as PayPal. Click for info --> Business Profiles Tax FAQ – Venmo
By the way our 97 & Up group has very active forum with a LOT of really good info on the subject of 1099s.
Use a service: