"direct:" "The administrator may issue your distribution in the form of a check made payable to your new account. No taxes will be withheld from your transfer amount."

How did he cash a check not payable to him?

"but the 1099-R is showing this distribution as a non-taxable direct rollover."

Exactly.

The employer amount typically is pre-taxed and would not qualify for Roth, unless he intended to do a conversion of it. It would be rolled into a Trad IRA account.

You would enter each 1099-R separately and on the worksheet, mark that one of them is a coronavirus disaster distribution.