The tool square to the chuck is mostly OK, but sometimes, especially on lighter machines, the tool may tend to draw in while cutting, so roughing with a tool with a lead angle may be prefered, or the tool cocked in the holder to provide a lead angle, then finishing with a tool in position like you show. Yes, CRS is best, much easier to cut than HR; if the piece does not have to be welded on to something, 11L14 is even nicer to machine.