I'd do all the turning then drill the two small holes. You can then poke a couple of pegs or drill bit shanks into the holes and use those to line things up when clamping the work.
Cut the radius with a boring head, at that radius you probably want the tool sticking out the side hole of a typical 2" boring head rather than the end. A flycutter could be pressed into service if you don't have a boring head.

Another option is to mount the work on the lathe cross slide and use a between centers boring bar to do the curved cut
