creating round holes easily

[Llama Juice]

Old video I made for someone, like 10 months ago with terrible mic.

Shows my method to this situation in Maya.

[FRain]

Boolean only works on non-sealed meshes, or else it just leaves fucking holes everywhere.

and especially fucked up holes if your mesh is a giant clusterfuck.

[BobtheGreatII]

So can you do this over and over to create smoother circles?