Recently I made and tested macro program which mill hole (ramping), and measure it's diameter.
After measuring, program repeats this two sections until the hole diameter is bigger than the bottom hole diameter, which is given in program.
It has to be tested with materials, because start offset should not be the same for aluminium, steel etc.
It's a good starting point which has to be tested for your purposes.

Take it for free - for any kind of macro programming, catch me on [email protected].
Renishaw number should be defined - I set 200 for me.

Best Regards