The IRS guideline requires a 1099 for all independent contractors/self-employed for any work $600 or more.
Changes to the Tax Cuts and Jobs Act of 2017 made stricter guidelines starting in 2018 where you are no longer allowed to claim any entertainment expenses (Sporting event tickets; expenses atnight clubs, theaters, country clubs, and other purely entertainment related charges that are directly related to the taxpayer's business. It used to be 50% but it is now 0%. Meals are 50%.