May be overthinking a complex PDF issue?

I am creating a set of PDF guides/forms that have some uncommon sets of requirements, and I think I may be overcomplicating the process, because I haven't been able to figure out a solution that meets all my requirements. Here's an overview of what I'm trying to achieve:

I have created a step-by-step guide for measuring and taping basketball gamelines in inDesign. That guide also doubles as a form. The first section of the form has inputs for the court name, size, start date, and supervisor name. Each step in the guide has 2-4 initial boxes and one supervisor initial box, to be filled once the work is done, and the last page has inputs for name, date, and signature of the lead painter as well as name, date, and signature of the supervisor. The guide (indesign file) also has a blank page reserved for attaching an image of the court design to be painted.

This form will be used for every court, so it needs to be somewhat easily reusable. We talked about the possibility of pre-filling the job name and somehow inserting the court design to the PDF each time before sending it to the subcontracting company doing the work, as a way to work around the lack of interactivity on mobile, as these forms will all be filled and signed on ipads at the job site. Where the majority of the complexity comes in is that in addition to needing a reusable pdf form that will be unique for each job (title, design, and court size), we need to have it e-signed, but not in the way that we're used to using e-sign. We don't know who the person filling out the form will be, nor do we know who the person signing as lead painter will be. We only know the supervisor for each of the subcontracting companies. However, the supervisor signature needs to be done AFTER the rest of the form has been filled and signed. Once the supervisor e-signs, it needs to be sent back to us as well as the basketball league.

Here are the issues I've faced:

-Can't add two different signatures on the last page without designating a second recipient (both signature fields update simultaneously with the same signature).
-We don't know who the person filling out the form (first recipient) will be, or whether that will be the same person as the lead painter.

-Adding court design images in acrobat is awful, and it doesn't detect the content frame from indesign. Editing the indesign file every time is not a viable option, since it means reworking the pdf in acrobat all over again, and I will not be the person customizing every individual form.

-There will be over 90 of these forms used over the next few months, and beyond that, a few hundred times per year AT LEAST.