So recently I have found a guy on craigslist that will haul off my tree limbs. He charges $50 for a 5x12 trailer load and even does the loading himself. So, I will stack the limbs at curb then he comes by and picks them up. He has a full time job, just does this in evenings and uses the municipal dump where they don’t charge him. So he thinks he is making $50 an hour. I have only used him 5 times so far (total under $300) so I know at this point I don’t need to 1099 him. However, I am keeping track of amounts paid and imagine I will keep using him past the $600 threshold. I plan to warn him that I will need to give him a 1099 form, but how do you educate a craigslist fellow on this? I don’t want him to think I am screwing him but also ethically need to make sure he understands what it is. He isn’t the brightest so maybe there is some other way?- especially since he has another job. Not looking to break any laws, just need best option.