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You don’t need to send him a 1099NEC.   You need to give a 1099NEC (previous a 1099Misc) to anyone you paid $600 or more to for the year. But not to corporations or for merchandise. You enter it under Contract Labor.  If you have the Home & Business version….. Go to Business tab- then Continue Business Income and Expenses - Click the Start or Update button   If you haven't added a business yet you have to go though a lot of screens describing your business.  Or if you already added your business, you should see the Business Summary page that lists your businesses, (right below the list you can Add Another Business)   Then click EDIT by the business name and the next screen should be a list of  topics, Business Profile, Income, Inventory/Cost of Goods Sold, Expenses, Assets, and Final Details last.   Under Business Expenses, Click Start or Update by Other common business expenses Contract Labor is the 5th item in list.  

There is nothing you get back based on entering a SSA-1099 on a tax return.  Unless you had federal income taxes withheld from the benefits during the year.   Please expand on exactly you are wanting to do.

The online editions are only valid for one tax return per account and User ID.  To complete another tax return using the online editions you will need to create a new account with a new User ID. You can have up to 5 online accounts with the same email address.

Self-employed individuals in a line of work that customarily and regularly receive tips are eligible to take the deduction and that includes hairdressers.  Make certain that you have the correct employment selected.    

@user17684268320 wrote: Any idea WHY it's taking so long? There could be issues related to the software being adjusted based on the legislation that was passed.  But really do not know for sure.  This sometimes happens either based on the IRS requirements or the legislation requirements.  Have seen this before since using the desktop editions for past 25+ years.  Sometimes this section is completed in December or early January, sometimes a little later.