I think you are really close! I actually spoke with the payer online and my new FA both and this is what they both told me...they are in agreement.
Looking at the details because it gives the most information...the box 5 ($36,000) entry in the 1099 is the amount of contributions we personally made into the after tax 401K. (It's technically not a roth, but kind of acts like one) The gross distribution of details (1) of $66,000 minus the employee contribution of $36,000 comes up with the taxable amount of $30,000 in box 2a of the 1099. I get all that. The details (2) shows a distribution of $33,000 and since none of it shows a taxable amount on the details...and no amount of that is included in box 2a of the 1099, the payer told me the entire $33,000 is non taxable.
Therefore, I believe (as does my new FA) that the $30,000 of taxable rollover into a traditional IRA...and the balance of $70,000 into a Traditional Roth IRA is correct. The difference between that $70,000 and the $36,000 employee contribution is the amount paid by the employer and included on a W-2. My next task then is to follow your instructions with splitting the 1099 to get the program to recognize it correctly.
Do you agree? And won't splitting the 1099 throw a flag to the IRS or won't they even know?
Thank you for all your help...it's been amazing!
