All these people making Uber money on the side ... the whole thing was possible in part due to the low friction in (and also complete disregard for) the regulatory environment. I’m in NYC and honestly can’t figure out how to legally hire a studio assistant for a few hours a week without being at risk for any of a number of lawsuit vectors. So I just coil my own cables. And I don’t mentor people who want to learn some…
You could 1099 them but considering the likelihood of someone who's taking an entry level music job claiming the income on their taxes seems like a recipe for an audit for both parties. Realistically you should probably do what everyone else does in this situations and pay under the table. Think of the lost taxes as billing the government for making stupid laws that can't reasonably be followed even when you want to…
Payroll might be complicated to learn the first time. But it's like riding a bike, once you learn it's trivial to do.