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I can't understand how your group is self hosting Drupal, some of these are so basic (such as matching NTS and x86/x64 of extension with your PHP compilation) that it leaves me puzzled and I hope this is a hobby for you.

- The Wincache backend settings are wrong. There is no /contrib/ level by default.

There is nothing wrong with this. You can put Drupal modules wherever you like.

- The newest Drupal core is able to install properly and does not require the patch mentioned for Drupal Core.

Yep... that needs an update.
- Also make sure you make a new Drupal WEB SITE in IIS. Not simply an application off of the Default Web Site.

You can do both of them without issues. Of course the recommended is one combination of AppPool+FastCGI Environment+Website per application.

- When you rename the Drupal settings file you need to leave around the default.settings file as-is or Drupal will issue a warning/error.

This is always like this with Drupal?

- Make sure for the pdo_sqlsrv extension you pick the version that matches your PHP (5.6 for me), is NTS, and has pdo in the name. Rename it to php_pdo_sqlsrv.dll

....
- You have to increase the pdo sql serv buffer max size or Drupal will give an error message. Add this line to php.ini:
pdo_sqlsrv.client_buffer_max_kb_size=24480

....

- PHP Tools seems to only be a 30 day trial, not sure what the best long-term free alternative is.

This is what really triggered me to write this comment. Writing good software takes time and money. The economy behind open source is complex, and "free" is never really free. You spent a whole day setting this up? Then that's not free at all, that's 1K ($1,000) at a standard Drupal developer rate for 10 hours of work. Maybe with the right tools, going through some paid trainning, or paying a consultant would have turned those 1K into a couple of hundreds. PHP Tools is extremely cheap and feature full, it will potentially save you thousands of dolars in wasted time. If you want a long-term free alternative you can use Sublime or Notepad. Those are "free", in the sense that you will pay with your time the lack of proper tools to work.