Convert each element of Text field to become Checkbox

Why not create separate assignments instead of attempting to create and add entirely new properties? (eventually your system would become clogged up with hundreds of more or less similar properties).

Edit: This also has other advantages: assuming the main object is a work order or similar with a workflow you could use the workflow engine to automatically transition to a All Jobs Done state once the worker has completed all separate assignments.

I would also try to teach the admin staff to create those separate assignments right away instead of trying to programmatically convert a text field.

Why not create separate assignments instead of attempting to create and add entirely new properties? (eventually your system would become clogged up with hundreds of more or less similar properties).

Edit: This also has other advantages: assuming the main object is a work order or similar with a workflow you could use the workflow engine to automatically transition to a All Jobs Done state once the worker has completed all separate assignments.

I would also try to teach the admin staff to create those separate assignments right away instead of trying to programmatically convert a text field.

Really appreciate your suggestions Martin
Creating separate assignments is a viable option, it becomes a bit challenging for non-technical staff to complete both the separate assignments and the Jobs as they are using the mobile version of M-Files.
Please let me know if you have some other advise.
Cheers