After getting increasingly annoyed about how dense the mesh was becoming as well as general annoyance about having to do yet more rework and the fact that some things simply didn't want to stay square, I threw that idea through a brick wall and decided to just extrude the nails like I was originally planning and hope it wouldn't make a mess.
Which meant first trying to get used to the extrude tool (press enter first, then move it, then switch tools because pressing enter again doesn't drop it, I don't even remember which program that habit came from).
The nails didn't make as huge a mess as I thought they would.