
So, I got this cylinder, right? This is the top view, by the way. Here, on this top face, I want to carve a rectangle. Nothing fancy. Just a rectangle. How do I do this?
As cool as online tutorial videos are — pre-recorded ones, and I suppose I can lump in live-streams open to the public as well — the problem is that there’s no back-and-forth between the person making the video and the person watching the video. Aside from the usual issues of “wait, what was that instruction again?” or the more frequent “mine doesn’t work like that!“, there usually comes a time when a question arises that is just a bit off kilter that can’t be solved by the narrow band of information covered in a tutorial.
Back to my square-hole-in-a-round-peg problem. In one of the videos I’d watched, I learned about dealing with cylinders, and how using a subdivision modifier doesn’t work so well with them. One solution is to inset the face a bit, punch out the center face (X, Delete Face), select the inner edge loop, and use Grid Fill. This fills that hole with a grid that is kinda wonky on account of the fact that it has to connect what was a circular face with a bunch of squares.
But this is good, because I selected a bunch of faces in the middle of that and deleted them. Then came the hard part.

I thought that I could connect the corners of the hole, two at a time, and create a new edge. Maybe then I could delete the warped edge that ran parallel along that new edge, and move the remaining vertices over to my newer, straighter line.
No. No I cannot. Snapping a vert to an edge doesn’t put that vert on the edge, which I learned after having moved all verts to all four new edges. Still, I figured that I now had a bunch of verts that were lined up along a straight line, so I deleted those four new edges, and connected the verts using F. Voila!
Except, also no. I had selected a bunch of verts (the empty ones seen above) and tried to mass-face them, which doesn’t work because it literally mass-faces them into one big face. So I had to delete those faces, select four verts at a time, and face each one.

So now I have a nice, clean rectangle in the middle of my cylinder. But I can’t help but feel that there’s a much easier way to have done this. Maybe, maybe not, but I have no one to ask.