As we all know, OS Deving on windows is a nightmare
Who said that!?
You could go with http://frhed.sourceforge.net/
and Visual Studio.
No one has to have GCC and Unix-like envirorement to create OSes... Instead you could have PE kernel file and your own bootloader, instead using Grub which takes 32 kilobytes of hard drive and takes one part of RAM.
Please do not continue this project in Visual Basic, as it's beginner's language, and try using Win32 C++.
Anyways, for everyone which dislike PE files, could use your OS deving IDE. Nice work
I could help you when you would write it into Win32 C++.
It may look hard to use C++ for GUIs instead of consoles, but it isn't, when you get enough experience.
I don't like Visual Basic either, it is a language to get your started. If he wants to develop a fully automated GUI IDE, I would suggest him doing it in C#. C# is very GUI friendly and you can create what ever the thing you want with it. C++ is not an option, you need like 99340 lines of code to just create one simple window. Why do you care about 32 kilobytes???
Coding your own bootloader right from the start is not an option, you need to have some detect assembly knowledge. Maybe after 3rd/4th revision of your OS you could do that and see how much you learned.
On-topic: for my "IDE" I use: sublime text 3, cross compiler, NASM, emulators, makefile and default terminal.
I had this idea once, even started working on it, but I stopped because it was too difficult and time consuming.