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Own the following:

Consoles: Atari VCS, NES, Sega Genesis, N64, Dreamcast, Playstation, Gamecube, PS2, Xbox, Xbox360, Wii, PS3, Wii U, PS4
Handheld: Gameboy, Sega Gamegear, Gameboy Color, Gameboy Advanced, Nintendo DS, PSP, 3DS

The first thing that ever stopped working for me was the Playstation, though I got a good amount of play out of it before hand. It still turns on but tends to skip and nearly freezes entirely when attempting to play a cinematic, making some games unplayable. Still, I was rough with it as a kid, it was somewhat early in the application of CDs in consoles, and worked for quite a while, so I wasn't that upset (not to mention the PS2/3 were backwards compatible so I didn't really need it).

After that was the Xbox 360 which broke almost immediately, followed by another that broke a year later and my current one that, as of a year ago, ceased to work yet again (as in I no longer have a functioning xbox360). If it had happened once I'd be more forgiving, but 3/3 has me pissed off, especially given the Xbox1 isn't backwards compatible.

Finally, as of a couple of years ago my original model NES stopped reading games reliably as non-top loaders tend to do (this was a safeguard against unlicensed games), but after getting a $5 pin connector thingy and spending 20 minutes swapping them out it works beautifully again... Lord do I wish my Xbox360 were so easy to repair lol, no hard feelings here seeing as how I got nearly 30 years of use out of it prior to requiring a Big Mac and fries' worth of repairs.

Otherwise, all of my consoles work dating back to the 1978 model of Atari VCS. Only the Playstation and Xbox360 seemed to have real problems immediately, with the NES inevitably encountering issues down the road if it's not a top loader.

As for handhelds, Nintendo deserves credit for creating some stellar, durable hardware in this field, as does Sony now as well. The only one I've had a problem with is the Sega Gamegear, and it seemed to cease working about a decade ago. The cause of this is from something called "capacitor rot", resulting from cheap capacitors that cease to function over time. The Game Gear is notorious for this. I already have my soldering kit and shall soon buy the kit of capacitors for both the screen and audio, but definite points off for perhaps the most inevitable failure of functionality I've encountered outside of the Xbox 360.

For the most part I've been impressed with the hardware behind consoles and handhelds, and really they've handled the transition from cartridges to CDs and complex operating systems quite well. The Xbox360, though, undoubtedly stands out more than any other in lacking reliable durability.