Who is the recipient of the 1095A? She paid, but who does it belong to? The banking doesn't matter. The tax rules matter.

This doesn't seem right: "took $20,207 from 401k early but $4k in taxes were deducted"

You entered the net, not the gross taxable? Taxes would be withheld from the Gross distribution.

I wonder about this: "it populates with $20950 in medical premiums" and then you show $20,990 Medical&Dental, which would be Care, not Premiums. Did he really have that much in Medical Costs?

I'm not sure this internet forum is the place to review this much detail. Do you have someone locally to mentor you?