I've used OctoPrint on Raspberry for a while and now I've changed it with Intel NUC, so i had to move OctoPrint to Windows. Installation was not very user-friendly, so i played a bit with it and made Windows installer package, which contains prerequisites (Python, VS Build tools, C++ packages) and automatically installs them. You can skip prerequisite installation by unchecking checkboxes if they are already installed (especially pay attention to Python).
Setup creates environment (fixed path C:\OctoPrint\venv), installs OctoPrint. Installation in general executes all the steps from OctoPrint install manual for Windows, so pc needs to be online during setup.
I also made a Windows Service controller, which allows to start OctoPrint as a Windows Service (starts on Windows Startup e.t.c). Service is started automatically after setup is finished. Service exceptions and messages are logged in Windows Event Viewer Applications folder.
Installer may be downloaded HERE if anyone wants to test or use it.
It's still draft, tested on my few pc's, so errors may be possible. Feel free to share your experience.