Well, Nathan finally got me so I need to make this challenge page. The questions seem fun enough, thugh, so lets give it a shot :D
I almost feel like this question doesn't apply to me; I was pretty much steeped in technology from the start. My grandfather was a system administrator, around when I was born my dad built PCs for a living. I had my first computer, like, my own, before I was 2 years old from what my mom's said? Ran Windows 95, had a huge single button trackball since I didn't have the coordination for a mouse. For the most part I played...well funnily enough I can just say that I played Humongous Entertainment games. Namely their Junior Adventures (mostly Freddi Fish and PuttPutt that I recall,) and a few years later Total Annihilation, which was published under Humongous' "mature" label: Cavedog. I still play Total Annihilation online, funnily enough.
Going a bit further into professional stuff, I pretty much knew I was going into software development from the time I was a kid. At 8 or so my dad sat me down with a book on C++ and Redhat I think...6? I didn't get very far. Later on I started in earnest with JBasic on Windows before moving on to Linux, learning C, and it all went downhill from there. Fun fact: I got tricked
into maintaining a Linux distro like 6 months into using Linux. I learned a lot that way.
Probably the best piece of tech I ever owned, or at least the one I look at fondest, is a Nokia N900. I think it's pretty obscure at this point, so let me throw out the pitch for you: it was a smart phone with a decent 4(?) row keyboard that ran Debian. It had a custom (gtk at that time,) ui which worked well, had a good camera, and I think to this day it's the only phone I've had with an FM transmitter option. If you were in a car with no aux jack (like mine didn't at the time,) you could just create a tiny FM station. It also had an IR port, so you were able to beam files or use it as a universal remote. It was easy to develop for since it was literally just gtk or qt if you preferred. The only really notable issue I had was that it only had 128MB of RAM, which was fine for 2009 when it came out, for reference the iPhone 3GS had 256MB and the 3G had 128. It just packed a ton of features and creativity into a small package. It also had the best messaging platform I've ever seen: the texting app used libpurple. I had access to xmpp, skype, aol, msn, yahoo, sms, I think mms, all from the messaging app. I think Meego (the successor,) had a similar setup, and Sailfish (the successor to that) tried it, but by the time Sailfish was relevant Skype had changed its protocol (and Jolla didn't support it anyway,) aim, msn, and yahoo messenger were dead, all the major xmpp servers had walled off, and they never bothered trying to support any of the modern chat protocols.
This is kind of a hard one. Certainly the one I use most is my laptop, a Thinkpad T420. I always have good interactions with my Dreamcast (this year's OCC machine, hopefully,) I've played a fair bit on my Vita and 2DS lately. I think the pick is actually my Kobo, mostly because it just straight-up does what it promises. It reads e-books. I can shove epubs on there and it loads them. It's survived a decent amount of travel, the ui refreshes about as fast as an e-ink display can. It pretty much just works.
I think somebody else already called it but color e-ink screens will be nice if they ever get closer to mainstream. Of course we already have them now, they're just rare. A lot of what I do is just stare at text so the low framerate of an e-ink screen wouldn't be that much of a hindrance for me in exchange for the upsides that comes with it. I'm not sure what else I could even go for: I've decided to never buy another car made after 2010. I upgraded to a laptop from 2013. I don't really touch current gen consoles in favor of when handhelds were a real category. Yeah, I don't really have a great answer for this. I'm gonna be pretty amazed if there's any new cool piece of tech in the next 25 years.
Ah man, I guess I have to do this now huh? Well, I figure the people I talk to are most are prahou and thedaemon, so go bother them :D