Daryl- I understand exactly what you are asking for. If you use Aspire to create your toolpaths, you can create a custom post processor that uses Y (or X) instead of Z. The machine will not know the difference. For safe Z you will have to retract Y to the same safe distance that Z would have to retract in a conventional setup. This is all easy to do with a custom post processor.
The custom post processor must set Z to a depth such that the side of the bit is exposed to the centerline of the indexer within the "cutting edge length".
For your bit definition you must use a "ball nose" with the radius of the tool. Then you will get the toolpath you need. As with any ball nose it cant get into the V's in Jacks drawing any different than a ball nose in conventional cutting.
Make air cuts until you are sure the post processor is running correctly, then go for it!
I have not cut anything in that mode, but had already thought out how to do it, I think it should have some distinct advantages over "Z" indexer cutting. Good luck, and keep us posted!
Hope that helps-
D
"The best thing about building something new is either you succeed or learn something. Its a win-win situation."
--Greg Westbrook