I've tried following the dev guide (still not successful) to compile a debug version of cpython 2.7 and a couple issues that I run into:

* The VS2010 vs VS2008 confustion - the docs say "most versions before 3.3 use VS2008" - what does it mean by "most"? The current cpython trunk seems to work only on 2010 (with a variety of fun errors).

* VS2010 is hard to download, as is 2008 - direct links would help

* nowhere it's mentioned that you need to run stuff from VS console

* the readme and the devguide disagree on a few points - readme seems to be better, but also not ideal

* the docs don't say how to get svn.exe (that is install tortoiseHG, but then select extra tools from somewhere)

* the build seems to require perl, despite claiming it's not

Other things are misguiding too, but fixing all of the above would be a massive step forward

Agreed. The PCBuild/readme.txt file should clear up a few of those points, but the docs aren't exactly beginner friendly (and by that I mean beginning Windows users, not beginning C developers).

We probably need someone to write a dedicated document for building Python 2.7 at this stage. The dev guide should only really be for versions under active development. Unless someone else gets there first, I'll look at making it more approachable.

I built 2.7.11 on Win10 last Jan 16 with MCS v.1500 32 bit.  I believe that is VS2008.  Besides TortoiseHG, which I think is great, I downloaded SlikSVN minimal client only.  I somewhat arbitrarily picked it from some svn list.  http://www.sliksvn.com/en/download.  A suggestion, with note that minimal client is enough, would not help.  Tested install with 'svn help'. With that installed, pcbuild + appropriate args downloads all external dependencies needed.  F7 in VS GUI builds Python binary, no Perl needed.  The docs, including readme.TXT, are much better than 3 or 4 years ago.  (At the time, there was an undocumented requirement, to run tkinter, to move/copy some tcl/tk files.  Zack fixed the build script to make manual step unneeded.)  Obviously still needs improvement.