You are doing good, Tim.
I went to college for a Systems Analysis degree....might be called and Efficiency Expert....with the emphasis on computer based systems. One of the 'rules' the drilled into us was to talk to the guy doing the job....all of the jobs involved.
One of the examples was for a dairy company that delivered milk to the doorstep. The class was in 1970 and that was rarely done any more then, but it was a good example.
The system required the driver to mark a sheet with the number of each item delivered to an address. The point was that these deliveries are done at 2am and if we don't ride in the truck, we don't know what conditions we are asking someone to record numbers in tiny blocks on a form. Is there a light in the cab? Is there a place to put a clip board? Is there anything else going on that would make the job a PITA?
When we did a project, we had to interview the instructor, telling him who he was for the interview and asking questions. Our grade depended upon how well we integrated the needs and concerns of everyone for the project along with how well the system gathered the information needed.
What might take me an extra hour or two to get it right all around would save everyone who had to do the job frustration for the life of the system.