Placing fillable fields on a pdf dynamically

I am trying to automate a process whereby pdf proposals are processed to add fillable fields. After adding the fields, the pdf will be passed to PandaDoc to be sent for e-signatures. While it is no problem to place fields using PDF.co at fixed locations, my struggle is to add fields or checkboxes next to line items in the proposal that change with each customer. There may be 1 to 10 line items for them to select.

You can search for text and extract the coordinates using PDF.co, but only one search at a time.

I’m hoping someone has some good ideas to accomplish this. One idea is the extract those line items and have CharGPT simply add signature boxes. Delete the original text from the pdf, and replace it with the generated text including the fillable fields. The problems is the dynamic nature of the line items.

For reference, the original pdf is generated from a reporting software that I cannot change. It only generates a flat file.

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