After accidentally running Blender from a native console, I realized a much easier way to setup Blender for iterating over features/bug development. My old Blender Python module reloader was becoming too unreliable in my codebase so it was a welcome discovery.

To easily reload Blender for development:

1. Set up the Blender UI to your liking to test your add-on. Mine happens to be the scripting interface but instead of the notepad on the left, I have the User Preferences view with the add-on tab open.
2. Save this as your startup file for Blender
3. Run ./blender.exe from cmd, bash, or Git bash to capture error output in the console without having to toggle it manually every startup.
4. Optionally, run while :; do ./blender.exe; done from bash or Git bash instead to continuously rerun Blender when it exits automatically.