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.

You can, but it’s pretty lacking in registers.

It's still not a PIC12.

The nes is a simple but extremely elegant machine. Assembly isn't a problem, since the cpu is very simple, I recommend playing with it.

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.

20 years next year.

I haven't even reached 30, yet that comment of yours made me feel old.

It's probably more confusing since the DS had several iterations, first one in 2004, then the lite in 2006, DSi 2008, DSi XL 2009. And then the 3DS having mostly the same form factor probably made the design feel new for a lot longer.

It did launch in 04/05, but it's only two console generations older than a switch.

Considering the switch is at the end of its lifespan, I’d say that’s pretty old. It’s like saying 7 years into the PS3 lifespan that the PS1 isn’t old. It’s old