Creating multiple categories in one cell

Question

I've been asked to amend someone else's spreadsheet for our use. In this file, we track progress on multiple jobs but the same questions get asked every week and they never look at the status update columns because they would have to scroll and hunt. I would like to add a cell to each row that has several "categories" within that one cell that are static. Kind of like headings, but then have the ability to type a quick one-liner response to each category.

I tried adding multiple rows and just merging the rows in all the other columns individually, so the other cells were the length of this new cell that is actually 9 rows long. But when I did this, the other cells would not wrap text so that all the updates were visible. I uploaded a screenshot of what it looks like now. I'd like to accomplish this without requiring individual rows of cells for each item and make these categories static with the ability to edit a response to the right.
Thanks in advance,
Darrell