My immediate reaction to the monitor not displaying anything is that there's a problem with graphics drivers. I don't remember if Ubuntu has a way to try/install with generic graphics drivers, I remember there being some kind of option to do with graphics that I had to select with Chakra (which didn't last a day) and Manjaro (which is what I'm using now) to make the liveusb work so I could actually install it.

Can you get into the Windows install?