LLC means nothing for taxes, he is either a sole proprioetor for taxes or some other business type.
You can not have a sub contractor that works in the business, by definition a sub contractor has his own business and works for himself
see the attachment, the IRS is hot on this
If you pay a contractor over $600 a year in cash or checks or inventory, then yes you report it on a 1099-misc at year end. Payments made by CC or paypal, etc are not reportable by you.