Hi Tom,
our plug-in VSR Shape Modeling 2.0 has a function called MultiBlend. This function creates a nice result here without the need to use several functions, or break up the hole into several surfaces. See attached pictures and .3dm:
VSR-Result.3dm(1.2 MB)
If you are interested, you can download a three weeks test version here: http://www.virtualshape.com/en/download
Let me know if you should have further questions.
@JimCarruthers maybe you want to have a look at this, too?
Cheers,
Michael