Sorry for the delay in getting back, since my last reply I learned my brother-in-law passed away very suddenly and we have had to focus attentions there.
In looking over your question and what I believe your trying to accomplish, can you clarify a few things. Are you wanting to be totally on the iPad or can you go back to your mac at some point? I ask this, because I found a cool " data merge" tool from here https://iworkautomation.com/pages/script-tags-data-merge.html . It uses the place holder text in pages along with a numbers document to insert values where ever you choose. I currently use this to support my wife her clinical teaching she does. She takes her iPad I the field and capture attendee data on a “jot Form”. This data is then saved to a Google sheet. From there, I open it in Numbers and I open a pages document / template for the certification document and then run the merge tool. It takes the data and fills in the info to the certificate, converts it to a PDF, then attaches it to an email to be sent to the respective attendee. The merge tool also creates a save folder for all the certificates, ( where ever you choose ) on your Mac. I send this to my wife to be then sent to accreditation agency for permanent record.
Now this is just a very high level summary of how this tool works. Here is a link, https://vimeo.com/280031885 , to a screen cast of the workflow in operation that I made to connivence my wife how much better this was compared to her filling out each cert individually and then emailing them.
In using your iPad in the field with a Jot-Form, you capture the data and then later run the merge tool to insert the data in what ever kind of report style you like, taking care to place the “place holder text” where each respective data point needs to go. This works with either a one word data point or a paragraph. I have successfully done with 50 words on the mental health form I built where client history was explained versus a checked box.
If your not locked into a preset report form, your Jot-Form intake form can be printed as a PDF straight for the web app with out needing the merge tool. But in reading your examples, you eluded to needing a more narrative style report and then you would need to create a form document / template in pages to then run the merge tool as detailed above.
I am uploading a sample of what the PDF form version might look like. Now this is just a sample, so your final report would reflect the data point your monitoring.
Now I can’t take credit for all of the workflow, that goes to Sal Soghoian for making the data merge tool available on the Automator website.