I felt the exact same way, still do, but I bought a new drive and installed Linux Mint on it (it's the most Windows like experience I've found). I kept my old windows drive just in case, but I haven't needed it so far.
The only time I ever used something that wasn't Windows was DOS when I was very little.
It's definitely overwhelming when trying to get certain things working that aren't natively supported, but thankfully those are few and far between. There's also a lot of people in the Linux community that are passionate about it, and tend to be very helpful.
You can always download what I think is called a live distro, and run it off a thumb drive just to test the waters. Nothing you change will be kept though, and it will be sluggish comparatively.
This map does not include any of the street cars, any of the light rail, any bus routes, any of the linked transit like the GO system trains or buses, it's literally just the the underground subway only. Which if that's what you want to compare is fine, but that's not what the title says. The title clearly indicates transit system, which should include most of that.
A good transit system needs a mix of above and below ground. Toronto used to have an massively extensive streetcar system that even went as far north as Lake Simcoe . Which has been dismantled and gutted over the years in favour of cars. That's part of why they built the subway in Toronto in the first place, to get rid of the street car network and make more room for cars.