If I use an individual for courier service should I report that on a 1099?

Yes, if both are true:

1) You're paying the individual for courier services provided to a trade or business. For example, if you pay a courier to haul a box of cigars from your house, over to Uncle Ned across town, that's not reportable on a 1099.

2) The total amount you pay to the courier equals or exceeds $600 in a calendar year.