Holy shit, how much does it cost to rent out your crystal ball for a few hours? Because you got it 80% right.
I was 19 or 20 back then, and Windows was my main OS - though I did have some experience with Linux as well (running several distributions for desktop use, as well as working with Cygwin and SFU on Windows), and I was a relatively proficient C++ programmer, having spent ~6 years of pretty much all my after-school time coding game engines.
So it's not that I couldn't make it work - I eventually did. But it was so rough around the edges that I gave up in frustration twice.
And yeah, these days, Linux is my daily driver (well, technically Emacs - Linux distros are just various flavors of Emacs bootloaders for me).
There is a difference between a calculator and a type writer and there is a difference between an office os and one for programming.
Using Windows and blaming Octave for Windows sucking is a rite of passage for everyone in a BSc program. I hope you got better and switched to a Unix.