More user choice here is actually an incredibly huge burden. Managing file associations across a range of versions, many of which can no longer be updated, is hard enough without offering options. Not to mention the extra user interface required.

Personally, I'd rather the options be third party installers or tools. There's nothing stopping someone making an idle "installer" that sets up context menus and default actions however it likes. It would probably break uninstall/upgrade scenarios for the core Python install, but at least it's not a burden on our (very few) volunteers to diagnose, fix and prevent.

If or when the shell extension takes over the context menu (currently blocked on someone volunteering to do the implementation and testing), it may be possible to have registry keys to change the behavior. But I wouldn't count on it being highly configurable - that's not the aim of the main distro.