Steve Dower added the comment:

The last time I saw collected data on usage (based on Visual Studio users), 
there was no clear majority of "number of interpreter versions", but 3 was the 
most common (2 and 4 were roughly equal, 5 and 6 were more popular than 1).

The nesting also makes it considerably simpler for the installer to handle, 
since there are totally independent components contributing to the file 
association. This is very difficult to achieve in a reliable way (wrt 
upgrades/downgrades/uninstalls/repairs/order-of-install/etc.), and having the 
context menu here is the best balance of reliability, usability and ease of 
implementation.

Using the shell extension to generate the menu would also work well, as that is 
part of the launcher and independent of any particular Python installer. It can 
also automatically un-nest the menu when it's going to be short enough, or show 
the latest version at the top and nest all others. Ultimately though, 
implementing that requires somebody's time, and until somebody is motivated 
enough to do the work, it won't happen.

So your suggestion is valid, it just isn't motivating enough for me to make the 
change. That doesn't mean someone else can't do it, and from a personal level I 
will oppose a straight un-nesting (as I'm one of the outliers who has 20+ 
copies of Python installed on my machines :) ), but I'm totally in favour of a 
well implemented shell extension to make it more complete and easier to use.

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Python tracker <rep...@bugs.python.org>
<http://bugs.python.org/issue27603>
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