Tool boundary suggestion

[sendithard]

As I am learning cam doing some 3d toolpaths I'm finding situations where I intuitively would love to be able to select tool center on boundary for one selection boundary and then tool inside for the 2nd boundary. I would envision a flip button that changes which one is which.  I could be talking non-sense, but something I just thought about recently.

[Steinwerks]

Yes this would be handy, although with unlimited boundary selection capabilities the potential for getting very messy is high, which is likely why it would need a lot of exploration and careful consideration.