Mail Merge multi row variable data spreadsheet into PDF

I need to merge a variable data multi page PDF doc.

The excel spreadsheet does not have all the merge info in one row.  

I am attaching a sample spreadsheet and sample result PDF.  

A few things to note -

1.) Each row in the excel spreadsheet is not necessarily a new form.   The "ID for 1095" controls whether it goes into the existing 1095 form or if it is a new form.  The Employee ID can also be used for this purpose.
2.)  The social security number should be changed to ***-**-5624, even though the spreadsheet has the full number.
3.)  In part 3, all the covered employees need to be filled in.  This is where the information is gathered from the spreadsheet based on employee ID.  Secondly, the selections from the spreadsheets for months covered should be converted from "Yes" to check boxes here.

I don't mind purchasing a tool/software to do this, if there is one out there which will simplify this process.  What complicated this is that the form is a PDF and not a word doc.

Any advice on how to tackle this would be greatly appreciated.  

Thanks.
Test-File.xlsx
f1095c.pdf
f1095c1.pdf