Steve Dower added the comment:

I do need to contribute some PEP 101 updates at some point, since the Windows 
build no longer resembles what is described there, but it's mostly about 
configuration.

* Install x, y, z
* Obtain extra externals
* Install signing certificate
* Configure non-default settings
* Check out correct repo/branch
* Run tools/msi/buildrelease.cmd
(Optional: install x, configure SSH key, run tools/msi/uploadrelease.cmd)

Since I can't release the PSF signing key or my own GPG key, there's only so 
automated this configuration can be. The "correct repo/branch/changeset" varies 
depending on the RM, and not all of the build tests are automatically verified 
(high chance of false positives that require manual inspection).

Probably the first thing I should do is put the extra externals (binutils, gpg, 
htmlhelp, redist and wix) onto svn.python.org with the others and grab them 
automatically. I can add checks for configuration (things like the eol 
extension not being enabled, for example) and the default build doesn't need a 
signing certificate, so that's optional too.

But the overriding point is, these things aren't required for most people, and 
automating them is going to be pretty restrictive. For example, I would have to 
automate it by detecting VS 2015 and failing if it's not there - otherwise you 
don't have repeatability - and that's going to prevent people using earlier or 
later versions of VS for their own uses. HTML Help is basically stable (a.k.a. 
dead), but gpg and binutils are frequently updated and locking them down is 
also restrictive. Also, people may want to use their own MinGW or GPG installs, 
while I don't want to do that, so the model I use for building would be 
restrictive there too.

Finally, so few people actually want to produce builds that I can do plenty of 
work to make it easy, and there may be major issues that are never discovered 
because nobody else uses it.

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Python tracker <rep...@bugs.python.org>
<http://bugs.python.org/issue25255>
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