Never done anything but I think the gameboy family is a good choice. Unlike NES or SNES which use assembly heavily, we can use C for the GBA. There are also great communities devoted for them.
Definitely. I guess one can climb the ladder by first programming the NES and then SNES and just go up, maybe even learn some Japanese to immerse in the life of a Japanese game developer in the 80s/90s. Could be a long but interesting side project.