Hey Terry, as a first step towards fixing the current 3.5 issue of not having Edit with IDLE at all, is it okay if the "Edit with IDLE" menu launches (approx.) "py -m idlelib.idle %1"? Currently the shortcut menu is part of the launcher - the "Open" item launches "py %1", so they'll be consistent.

An expanded menu like Liam's mockup is possible, but I can't guarantee I'll be able to get to it in time. (It may also be better as something configurable within IDLE anyway - https://msdn.microsoft.com/en-us/library/windows/desktop/hh127424(v=vs.85).aspx describes how it can be done purely through the registry on Win7 and later.)