Every time I try to open a .py file from the Finder (macOS Sierra), IDLE opens up and then immediately "unexpectedly quits." I can open them from within IDLE without the same problem I've attached Apple's crash report. Additionally, in the Console I get an error message like "IDLE[14872]: objc[14872]: Invalid or prematurely-freed autorelease pool 0x7f81bf959048." every time the crash happens I am using Python 2.7.12; I installed the correct version of tcltk (something that is frequently mentioned when I search online for this problem) so that isn't the issue.
From the crash report, it appears you are using a Python 2.7.12 and Tcl/Tk 8.6 installed from Homebrew. The crash appears to be happening as a result of the Open Apple Event from the Finder to Tk. At first glance, I'm not able to reproduce the crash using a python.org 2.7.12 with an ActiveState Tcl/Tk 8.5.18 also on macOS 10.12.1. I don't have a Homebrew installation handy to test with and I don't really have time right now to dig into it but I think it very unlikely to be an issue with Python itself. You might want to open a Homebrew issue and/or a Tk issue.
The ultimate solution was to uninstall homebrew, since there is no obvious way to get it to use the right version of Tcl/Tk (8.5.18). And then to install the python binary from python.org, which does pick up the right version of Tcl/Tk. I can't remember why I was using homebrew, but the instructions at https://www.python.org/download/mac/tcltk/ (where you get pointed from IDLE) were a little unclear. I didn't realize that "if you are using OS X 10.9 or later and a Python from a python.org 64-bit/32-bit installer" didn't refer to the Python that came with macOS, or that I had to (or even could) install the python.org binary on top of the Python that was already there.
I'm glad you got it working. The information at https://www.python.org/download/mac/tcltk/ pertains primarily to using Pythons from the python.org installers; it doesn't directly apply to Python instances built by and supplied by third-party distributors like Homebrew or MacPorts. So there is nothing wrong about them supplying and linking their Pythons with their own version of Tcl/Tk, be it 8.6.x or 8.5.x. It would be good to figure out what the problem was that you saw and whether it is a general problem for other Homebrew users but that is out of scope for this tracker.
