Recommend to NOT use the 1099 entry sheets; instead total and enter directly on the actual line of the correct form.

LLC is a disregarded entity (same as the self-employment) so SSN vs EIN does not matter.

I like to create a supplemental list for my records (and share with client but not with IRS) 

necessary to enter 1099R

If he forms an S-corp he needs to contact those who pay his company & get them to use EIN.