Since different people have different ideas about what is retro, and I never tried to be a retrogamer, I just kept playing what I liked, I am going to just go with some of my experiences from the past.
NES- I loved many of the games, and was happy that I could play them at home and didn't need a pocketful of quarters. It sucked when we rented really bad games. Luckily I don't think we owned too many of the bad ones, however there were many that we rented that I really wanted to own (Duck Tales, SMB3) When the NES belonging to the family across the street occasionally had the problem that the frontloaders became known for we tried a bunch of stuff to fix it. We never thought it would get as bad as it eventually did, or that we were making it worse (in addition to blowing in carts, someone in the neighborhood had an NES Game Genie). It would be interesting to experience all that again with my current knowledge. Many years later I had a friend (or maybe a friend of a friend) that at least sometimes lugged around an NES in her bag. We were a bit different than the others in our social circle, and while others would be drinking and partying and being social, we would sit and talk about things that would bore the others, if they could even make sense of our off the wall view of the topic. When she pulled out the NES we went and hooked it up to a TV and had fun our own way.
Atari VCS/2600- I went to my uncle's house at some point after we got our NES and saw my cousin playing something. I don't know if she got bored, or just wanted to let me try it out. It looked bad, but it was a video game. Even the console looked odd, and not as sleek as our NES. I think I tried to play something but couldn't tell what was going on. I wouldn't appreciate this until much later.
SNES- The spoiled "rich" kid down the street that always got everything he wanted and had a huge NES game collection got a Super Nintendo right after they were released. The rest of the neighborhood kids were pretty jealous, but those of us that he hung out with got to play some games. Later, after moving, I remember being upset with the Mortal Kombat ports after having spent hours (days?) playing the arcade version, but some people I knew had a way to fix that.
Genesis- I had a friend that got caught up in the Sega Vs. Nintendo console wars around the time it was released. He felt that even Mario, as a mascot, was far inferior to Sonic only because of the Sonic games, and ignored the fact that we had played SMB games for years and had loved them. There was that little thing (red pixels) that I felt added to the experience of my Mortal Kombat experience, however I eventually decided that none of the console versions were as good as the arcade version, and I returned to pumping quarters into the machines at the laundry place near my school to play the "real thing" when I could.
Game Boy- At some point shortly after it was released I got a GB as a present. I didn't have many games, but Tetris was awesome, so it didn't matter. I had one of the black and pink fanny packs, and found that it was not really suitable for keeping my GB and carts safe, but I used it when I had to. As my game collection grew I started trying to keep it with me all the time, and every spare moment when there was light and batteries I was playing something. I found out that my father had one as well. His was in much nicer shape (screen cover still present) not due to him taking better care of it, but because he barely played it. His games were ok. The real treat was that he had one of those things you would slide over the top half that lit up and magnified the screen. Sure, it also had better (and stereo) speakers, but I could play in the dark! (Too bad I couldn't use the light nd my Game Genie at the same time.) Batteries obviously remained a problem.
Game Gear- I never owned one myself. It was cool that my friend that had one (I think it was the one I mentioned in the Genesis memories above) could play nicer looking stuff, however he never took it with him when he left the house because of the battery issue. That seemed completely useless to me, so I grew to love my GB even more. It pretty much faded from my life until a little over 10 years later when I found out someone else I knew had one. I am not sure why she kept it since I don't remember ever seeing her play it. During that time I had picked up newer versions of my own preferred handheld.
Game Boy Color- Color! I can even add color to the old games! I got the clear purple one, and it did everything I thought it would. It used less batteries, which was great, but it didn't matter since the screen was even harder to see than the original. There was a roadtrip that I went on and had both my GB and GBC. The color was nice when I had good light on my side of the car, which was really hard to get since it seemed the screen did this weird reflection thing making it hard to see even with direct sunlight...so I was still playing on my old GB sometimes. By this point I could play Mortal Kombat on my handhelds, but the games were even worse than the SNES and Genesis ones. It was cool that I could change the colors to make Link's Awakening look more like I think it should have, however due to the display issues the colors that worked best for me were not the ones I thought looked "right". Sure, I could have picked up the DX version, but it lacked the glitch I liked to play with, and I already owned the original. That screen, though. A blessing and a curse. The friend that carried around the NES was also fond of the GBC. I found this out a couple years before I started modding Game Boys, and it inspired me to start collecting them, and led to me making music (for myself) with them.
N64- I don't remember when I was first exposed to the N64, however the first time I really wanted to play was when I was visiting family and saw GoldenEye 007. I wasn't really into James Bond, but I was into FPSs. I didn't get to play much at that time, but I decided I would try to get a N64. I did, and eventually found Perfect Dark, which was much more my type of FPS, even if it wasn't all that different from GoldenEye. Someone acquired the expansion pak for me, probably around when Ocarina of Time was released. That game was good, but I still prefered the older Zelda stuff. Perfect Dark was the real reason for me to have that expansion pak. I rented the game once and told them I lost it. I still have that cart, and all of my original save files backed up in 3 different places. I love that game.
PlayStation- While I was still mostly into what was available for Nintendo consoles, I had a friend that was really into the PS. I never really played it except when he was looking for someone to play with. Sometimes I played a bit of FF7, but I didn't get into it too much. I liked some of the games, but I wasn't going to go out and buy one, especially since my friend was telling me all about the PS2 when I decided there were some games I wanted. The big problem was that Sega, which was no longer a company I gave much attention to, had something to offer.
Dreamcast- My first time seeing this thing was at work. A guy and his girlfriend brought it in. Even before they hooked it up to the TV I was a bit turned off by it. By this time (1999 or 2000) I was not willing to give Microsoft my money, or support them indirectly. I really liked the games, although the controllers seemd liked they were designed by a moron. Things didn't seem like they would work out, so the Dreamcast would not be the first Sega console I would own. What? You say I can burn copies of the games? Hmmm, maybe...
PS2- The friend that was super excited about the PS2 was following all the rumors and news, and he would tell me every little bit of information he found out. He showed me specs and stuff. All that was nice, but I think the reason I bought one was the backward compatibility, so I could play older titles I liked, and because I could watch DVDs on a TV instead of my laptop. While it was/is an important and impressive console I did not have the same feelings for it as I did with all of the others on this list. I think I looked at it as less of a console, and more of a media presenting device. It just didn't do it for me. While I was traveling around the world someone brought their PS2, which really confirms this for me, since we used it for evrything.
GBA SP- At the beginning of my period of bouncing around the globe I wanted a way to have entertainment. Sure, we would have access to generators sometimes, but there were so many unknowns that I had to think about my choice. I didn't want to destroy my PS2, plus it wasn't very small, and adding a TV or other way to use it on the go...actually, you couldn't use it on the go, but even when trying to make it portable it was too big. Obviously a handheld was the way to go. My Game Boys in the past had served me well, so I looked at the GBA. It looked like it had the same problems as the GBC with the screen, and I knew I would want to play in the dark. The GBA SP had a frontlit screen, but I couldn't pick up batteries everywhere. My decision was based on the clamshell design, that it was much smaller when not in use, and I didn't have to have a bunch of other stuff (like a light) to use it. I got some spare batteries, and with everything I had it still took up less space than an original GBA in a case with everything to use the GBA. I owned an mp3 player, however I would want a way to watch movies since most people didn't like what I was into, so I got a portable DVD player that could handle everything I wanted to throw at it, including mp3 CDs (this choice was made so that I could lose the DVD player and not have any major losses, such as if I took a laptop...plus I worked with computers all day, so I didn't need my own). Everything combined was still smaller than a PS2. The first time I was playing a game and saw someone else playing on a GBA I knew my choice was the best one for me. He was fine until it started to get dark, and I could close my SP and easily shove it in my pocket. A handful of us would play 4 player games since there wasn't a need for more than 1 cart to do this for some games. The only multiplayer handheld games I had played prior to this was Tetris and a bit of Pokemon, and those were nothing compared to what we were playing. Warioware was really fun, too. I eventually bought my first flash cart for my GBA SP. While I think the SP was sold to help buy a DS for someone, I used my flashcart during the early days of DS homebrew. That flashcart sits with my other stuff, having been replaced by a more modern one (although some titles, like my Metroid games, I will only play with the original cart). I have picked up an original GBA since it feels better to me, and if I really want to play a GBA game in the dark I use my DS. The DS and DS Lite accompanied me on later trips, and I did start taking a laptop.
I am skipping some stuff since they aren't as retro, but I wanted to mention one little special one that follows in the footsteps of my other handhelds, even if it is still alive and seems to be selling well when it is available:
Pandora- I don't remember exactly how I first found out about the Pandora. It was still not close to being released. It seemed like the perfect combination to me, a little Linux computer that I could play a bunch of games and emulators on. I knew someone else that had picked up one of the earlier open source handhelds, but my Nintendo stuff was enough for me back then. Most of you know what happened with the Pandora. I would check in from time to time, and took forever to buy one. When I did I was surprised that it looked and felt a lot rougher than things from big companies. This made me happy, since it told the story of how it came to be, and it was made to be used, not to look pretty. It does a lot more than I expected, and unfortunately I use it more for work and web browsing than games. It fit in perfectly with my family of old consoles, handhelds and computers, and resembles to me some of the stuff I have from the 80s. While sitting around I could play a massive library of games, and if I got bored I could find trouble to get into on wireless networks around me, or be productive. If I know I am going to be out for the day and possibly sitting around my Pandora is the most likely device to accompany me (it does more than all the others combined, with the exception of a few methods of communication). My Pandora will be staying with me, and I am really looking forward to the Pyra.
Since computers were mentioned in the OP, so I will talk about one old model:
Apple IIe- This model of computer was present with me from elementary school, through high school, and beyond. I did play some educational games on it in school. It was not alone at my schools, and there were often IBM compatibles and Macs. The Apple IIes stood out for me because they reminded me of my earliest interaction with computers. I felt like I could get them to do what I wanted, unlike the others in my schools that offered me a handful of options. Even as late as 2000, when I last saw a IIe in the wild, I more often saw them with monochrome monitors, so even that is a big part of the experience to me. With them, although it is a part of it (and I have some odd stories of it), my memories and what I used to do are less important than the idea and the freedom they represent to me. When I learned that Apple used to support users doing what they wanted with their computers by giving them a information, it fit with the direction I was already going in. I did come across some Atari computers at the homes of friends, and I am sure some people had C64s that I never saw. The Apple IIe was how computers should be, for me. Maybe I couldn't get all the games and software that I wanted to use for them, and perhaps things weren't as flashy and nice sounding, but that was ok. If I wanted to make it better I could. I have no doubt that I would feel and think differently about all of this if I had a computer at home when I was growing up that I was actually allowed to use. Schools and libraries were where I went to learn and do what I wanted, so even if I am a terrible student, I probably learned much more in school than most other students. It may not have been what I was supposed to learn, but it helped me become as I am. There was almost always an Apple IIe present, so they played a big role in that.
