PAL kid here! I got my first transparent GameBoy pocket with a copy of Wario Land when I was about 6. I then watched in envy as my classmates upgraded to GameBoy Colour, but then when I was around 10 my grandma upgraded me to a GameBoy Advance, which I thought was the coolest thing ever because of the oval design (still my favorite handheld design). My brother would borrow it for days at a time without giving it back, so eventually she gave him a GBA SP since the old model was out of stock, which of course meant she had to give me one as well :P then when the original DS came around, which I again thought was an awesome piece of tech, my mom (I think) helped fund that one.
Fun thing is, with DS and Super Mario 64 DS in hand, just for a bit, I was the cool kid in class with the newest hardware. I remember one in-door recess where I let it pass around and everyone tried out the various mini-games it came with.
(...what I wouldn't give to do grade school all over again...)