How to do his position? The potential problem you run into is he could go to the dept of labor in whatever state he is in and make the case that he is not actually a contract employee, but a W2 employee and deserving of benefits. Granted if it’s a part time position, that’s also a different matter. You could also get yourself in a pickle if you were to give him paid time off. You could give him a bonus for good work and call it that and not get into trouble. At least, this is my understanding. I am not an HR person and have always hired people that know more than me about HR for those roles.