Tax Year Prior to 2020: Payment issues and help

Could you please clarify what type of payment issues you are having?

I run a small forestry operation and I hire workers for sums of 50 to 300 dollars. Do I need to issue a 1099?

Thanks

Who are you required to send a Form 1099? You are required to send Form 1099 to vendors or sub-contractors during the normal course of business you paid more than $600, and that includes any individual, partnership, Limited Liability Company (LLC), Limited Partnership (LP) or estate.