Early 1980s:
A monochrome LCD handheld with a Space Invaders clone, similar to this:
Besides that I frequently played on some arcade machines (f.e. 1942 + Outrun) and a lot of pinball machines. At my best friend's we were often allowed to play with his Atari VCS (Pong, Pac-Man, Space Invaders, Q*Bert, Atlantis, Frogger, Jungle Hunt, Defender, Pitfall, Moon Patrol and Pole Position) when the weather was bad... otherwise we had more fun playing outside without electronic gadgets.
Late 1980s:
At 14 I had saved enough money for a Commodore 128 + 1571 floppy drive + Commodere 1702 color monitor + an Epson dot matrix printer (of course I needed it for school!).
Additional to the color monitor (much clearer picture than the old TVs) i bought a TV-receiver so I got independant to the family TV.
Here is a ~30 year old "blast from the past": two pictures of the desk in my old room in 1989 (the photos aren't well preserved unfortunately):
The C128 ran mostly in C64 mode, but I loved to program in Basic 7.0 these days, so the additional expense wasn't a waste. Numerous text adventures and especially Maniac Mansion and Zak McKracken had sparked my love for the adventure genre (still my favorite genre) and since most games didn't have a German translation, my English skills improved quite fast.
While reading the test of "Indy 3" in the PowerPlay 10/89, I made the decision to save money for my next computer: an Amiga 500. I couldn't even think of a sinfully expensive PC at that time. I didn't had a sponsor in my family for home entertainment, so I had to buy all my electronics myself (including my stereo, walkman, discman, VCR, TV...), but that's okay.
Early 1990s:
When I finally had the money together, Monkey Island and Loom were already released. So I bought an Amiga 500 + 1 MB memory expansion + Commodore monitor 1084 S. Later I "pimped" my A500 with further upgrades (f.e. two external floppy drives, a turbo card, another 8 MB RAM, a Kickstart-Switch for different ROMS were added)... perhaps I should have started with an A2000 in the first place 
I often played Super Nintendo and Mega Drive with my friend and was even allowed to lend these systems and all his games for weeks... my favorites were the Donkey Kong Country games.
Mid 1990s to present (PC):
The next impulse for a new computer was given again by a LucasArts adventure: Day of the Tentacle (and Wing Commander, which was playable on the Amiga thanks to the turbo card, but not really fluid). My first PC was a 486 with 33 MHz + high-quality 15" monitor (the image quality was always very important to me), later the CPU was upgraded to 486 DX4/100 MHz.
This was the beginning of the hardware spiral, especially with the graphics cards I was always up-to-date: I bought the first 3dfx card (Orchid Righteous 3D) right at launch, then Riva 128, Riva TNT, Riva TNT 2, GeForce 256 DDR, GeForce 3, GeForce 4 Ti 4600, Radeon 9800, Geforce 7800 GTX, the almighty 8800 GTX, GTX 275, GTX 460, GTX 580, GTX 970 and GTX 1070.
Due to smaller performance gains I don't change my CPUs that often since my first dual-core, also the bottleneck shifted from CPUs to GPUs decades ago: 486/33, DX4/100, AMD K6-266, Celeron 400, Celeron II 875, Athlon XP 2000+, Athlon 64 3400+, Core2Duo E6600, Core2Quad 9550 and i5 4670K.
Monitor replacements got even fewer: after a 17" monitor, the Iiyama VisionMasterPro 501 (21") had served me well from 1999 to 2007. From mid 2007 to early 2018, the Dell 2407WFP (24" with S-PVA panel, 1920x1200), supported with a 120-Hz Acer-monitor from early 2011 to early 2018. My new main monitor is a HP Omen 27 (G-Sync, 2560x1440 @ 165 Hz), my good old Dell was downgraded to secondary monitor and the Acer was an upgrade for my brother's PC.
Here is another ~20 year old "blast from the past": a picture of my PC room in 1999:
And another 10 year old "blast from the past": a picture of my PC room in 2008:
And another 6 year old "blast from the past": a picture of my PC room in 2012:
Mid 1990s (consoles):
Parallel to PC, I had and still have a lot of fun with all the consoles and handhelds. I played Atari VCS and SNES before (see above), but my first own home consoles were the PlayStation (1) and the Nintendo 64... actually I bought both together with two friends and everyone got his turn. Eventually, both systems and all their games ended in my place, because both friends focused on PC gaming and lost interest in the consoles.
My PS1 is still connected to my good old "black trinitron" Sony CRT in my retro room and ready to go (alongside all my other "pre-HDMI consoles"):
But nowadays I prefer playing PS1 games on a much smaller screen: my Vita.
Late 1990s/ Early 2000s (consoles):
I have to admit that after the 5th gen I wasn't very interested in console gaming for a while... I had more than enough great games to play on PC.
I never bought and played a Dreamcast (I'm playing Shenmue 1 for the first time right now). I never bought a PS2... but I borrowed another friend's PS2 months (I have such great friends when I think about it!).
In April 2003 Nintendo brought me back: I bought a "GameBoy Advance SP Silver" for a planned long vaction (my USA West coast trip). It included a €50-coupon for buying a GameCube:
The GC was already cheap at that point, but thanks to the coupon I got the black "Metroid Prime" bundle for only €144 (including the console, the game, shipping and taxes).
In March 2004 the original Xbox followed... I bought the pretty "Crystal Edition":
Mid 2000s to present (consoles):
After that I bought all handhelds and home consoles, beginning with the awesome PlayStation Portable in April 2005. Similar to the GBA SP, I bought it for my second USA trip (the East coast this time). Since it was region free, I imported the "PSP Value Pack 32 MB" for a very good price (€150 instead of €249) from Canada and got it months before the European launch.
In November 2005 the Xbox 360 was my first console I bought on launch day and IMHO it had the best selection of launch games in console history. I preordered it in the next "Saturn" market and waited together with a big crowd in front of the store until it opened.
In November 2006 the Wii was my second console I bought on launch day. Since i didn't enjoy the "experience" of waiting in the cold the previous year, I preordered the Wii and "TLoZ: Twilight Princess" in a small toy store in my home town and picked it up after work... much better! All hardware after 2006 was ordered online and delivered to my home... even better!
When the PS3 launched in Europe in March 2007, I was going to wait for a long time... too few exclusive games, since I already had the Xbox 360 and a good gaming PC. But just three months later, I got it as a free bonus to a very attractive mobile phone contract. Over the years it has replaced the Xbox 360 as my favorite 7th gen console.
In December 2008 I bought a black Nintendo DS Lite to catch up on the best DS games and fell in love with two third party series: Professor Layton and Ace Attorney. Wasn't impressed by the hardware compared to my good old PSP, but the games were fun nonetheless.
In the summer of '69 2010 I got another great mobile companion: my first iPad. I love that form factor, it is great for point & click adventures (my favorite genre, see above). A lot of good games were ported to it, especially in the first years, and the software prices were wonderful (in-app purchases weren't a thing back then. The Infinity Blade series and some other games were technically impressive and well suited for touchscreen input. Over the years I added a few other tablets (Windows, Kindle Fire, Android), but the iPad series is still my favorite.
2012 was another handheld year for me: i bought my first PS Vita (OLED, 3G) in February and the 3DS XL at its launch in July. The original 3DS had a lot of design choices I didn't like and I'm glad that I waited for the XL-version.
In the last week of January 2014 both the Wii U Premium (Nintendo Land bundle) and the PS4 (Killzone bundle) arrived at my home.
In 2015 I added a PS Vita Slim and an Xbox One to my collection.
In October 2016 the PlayStation VR opened my eyes to a new dimension of gaming, one month later my PS4 was replaced with a PS4 Pro.
As a new VR fan, in 2017 I bought an "Oculus Rift + Touch controller" bundle in the "Summer of Rift" (first big price cut)... also a PS Aim controller together with Farpoint.
Last October I finally bought a Nintendo Switch... I was planning to get the red "Mario Odyssey" bundle, but then got a good deal for the normal red/blue version and the pinkish Xenoblade Pro controller. This year a LAN-adapter, a 200 GB microSD card and a Zelda controller for guests completed my Switch setup.
