As one of the "Kids" being talked about n this topic, as I am currently 17 I should through in how I got into retro gaming.
My first game console was a Game Boy Color, I got from my cousin when she got a Game Boy advance SP. I mostly played licensed games, like Tiny Toon Adventures and Animaniacs, I loved those shows, I saw them in syndication on Nicktoons Network. I did not know much about Nintendo or retro games, I had Pokemon Yellow because I watched the show, but sucked at it because I did not know I had to level up my Pokemon, and I stupidly gave it away a year or 2 later. I persuaded my mom to get me a PS2, I remember being existed by how much complex and better Spongebob games where compared to the point and click PC games. My friends had Gamecubes and I new somethings about Nintendo characters, but I though Samus, or as I pronounced it "Samerus" was a guy. I was into Sonic, because he was the only game character I reconciled on the PS2, I did not know much about Crash Bandicoot, Sly Cooper, Ect. But I dd have Racket and Clank and Jak and Dexter, which came with my system. I remember thinking "Shadow the Hedgehog " was so cool because he had guns. I had the Sonic Mega Collection Plus, so I played a lot of the retro games, but I did not take much interest in retro games yet.
For Christmas I go a DS Mario Kart bundle, this was in elementary school, I think 4TH or 5TH grade, and that is what really sparked my interest in Nintendo. Through the Internet I found about the NES and the original SMB trilogy. I later got SMB Deluxe on the GBC at a tag sale and loved that game, I think I remember renting it from Blockbuster before that. I also got Super Mario 64 DS, I saw it in Gamestop and was confused by the title, but the clerk told me what it was. I think one website I went to was "The Mushroom Kingdom" for Info. I alos later found the AVGN. I also remember using emulates a lot, I had this program "Console Classix" that had almost every NES game and Atari 2600 game free, There was a paid subscription thing that let you play SNES, Genesis, Game Boy Ect. It was fun going through the list and playing random games, I found Kirby's Adventure and loved it. When I got a Wii a bought that and Super Mario Bros on VC.
My first older system I got was a PS1 at a tag sale for $15 It came with a few things. I saw a N64 controller on the table and asked if they had the system and the lady came out with a PS1 she found, close enough. I got it it September 20, 2009, I know because by then I had Facebook and did a post, here is a pic.

I found some boxed NES and SNES games from a old video store, I got Pro Wrestling, Battletoads in Battlemaniacs and ether Gods or Lagoon for $5 each. I recently went back and cleaned them out of non sport titles, all where covered in dust. I found Tecmo Bowl at a dump on the ground, It was cracked on the front. I was happy but did not own the systems. I wanted to get a FC Twin, never did.
I later got a Orange N64 for free from a friend of my sister. It had no wires, 3 controllers and some wrestling games. 2 of the 3 controllers had broken analog sticks. I bought cables later off amazon. I made one of the broken controllers into a Flash Drive. I brought it to school sometimes.

I later got a SNES with DKC 2 and Strike Gunner STG, It worked and then it did not. I got a game bit and opened it, It was full of cockroaches.

I cleaned it and I worked. I almost got a Dreamcast but his dad through it out or something. I later got a NES (eBay), Genesis (Amazon), Atari 2600 (Crag's List), 3DO (Good Will)