Hi Ben,
The “Subdivision Surface Object” [SSO] has two settings, for editor view and for renderings in the picture viewer. You can set them up higher if needed to gain a round edge.
My opinion, as you ask me, if the “supportive edges” are done nicely, the result can be sufficient, but perhaps only with a high SSO setting. However, the main concern on my side would be always, if the SSO is useful here with adding to the whole model so much more density, or if a 12, 16, or even 24 segment solution would work better. So the overall SSO value can be lower. The higher pre-defintion meant of course always with the idea to reduce it before it hits other areas. This is certainly a judgement call of time investment during modeling vs rendertime.
I would not just dumb an SSO into the scene with a high setting and try to fix something that I could do in a certain amount of time with some modeling.
There is also the idea, that one lowers the SSO values to be able to work fluidly, but pays the price that edges are not were they will be during rendering. Again, this is were a modeler become a job definition in its own rights.
All the best
P.S.: I have done a whole series about holes, based on a master-class a while back. Perhaps some tools are missing back then, but perhaps some “stuff” might help.
http://www.cineversity.com/vidplaytut/industrial_modeling_-_holes_part_01
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Way back in time, I did a cylindrical hole cu tutorial, but it is really old:
http://www.cineversity.com/vidplaytut/modeling_02_cylindrical_hole