This would never fly in my State: "(W-2 secretary during the day; 1099 occasional cleaning person at night). That's perfectly legit."

First, unless the person has a cleaning business and cleans at other locations, too, and is using their own supplies and tools, then all you have is an employee with multiple tasks or duties. Next, our Worker Comp service is run by the State, and they have issued guidance on this specific subject, that you have no way to show "when" the person hurt their back while on the job, no matter what worker classification someone tries to apply to justify a 1099-Misc along with a W2.

It's not unusual to issue a 1099-Misc for box 1 rent to a mechanic with their own tools or a trucker for the use of the truck or renting their fifth-wheel trailer for on the job needs. You also see 1099-Misc for lawsuit settlements. It's pretty easy for the person to look at their W2 compared to what they know their wages should be, to see if this 1099-Misc is part of it, or in addition to what they expect their gross to be.