If I had to pick an era, it 1981-1997. Basically, everything from the 8088 up to the 486, with some Pentium thrown in. Honestly, I don't find any nostalgia in anything beyond that because I spent the better part of the 2000's fighting with so called "Geeks" and "Nerds", some with merit being Network or Systems Admins, over how "useless" that old hardware was - met with rebuttals like "What are you going to do with it? Play Pong? Write Snail Mail?". So from PII to about Pentium D era, it's not nostalgic, in a way, that was the "enemy".....and I felt like that's when hardware really lost it's "soul". Those old machines had some crazy personality to them, and there was almost an interesting informercial-meets-ham-radio-hobbyist vibe to them that I always thought was incredibly cool, add to that all the constant media brag about "scientific technological advances" and then "XT/AT/286/386/486/Pentium" tied to it, and it makes it cool. Plus the fact nobody was talking about brands on the scale of now when it comes to everything gives it a fun mystery to figure out.
When it comes to games, the first PC game I ever played was Microsoft Adventure - on a Tandy 1000 SX, and I was quite good at it. That said, it did not do much to really enthrall me with the PC, here I was, 16-bits of power, on an 8-bit bus, and this thing could'nt even put graphics on screen (or so I thought at the time) like my lowly Ricoh 2a03 Nintendo or 6507 powered Atari 2600 could. Yet somehow, at school, the IBM PS/2s could eek out 4 color CGA with Reader Rabbit. But I still enjoy those really really old DOS Games sometimes like Burger Blaster - which I got from my auto-shop teacher in high school who had an original IBM PC 5150, which I was the only guy in class who knew how to use, let alone LOVED dragging big box DOS games into class to play on it (we had just moved to block scheduling and had more time than class could use, so I'd play Ultima V for the rest of class, or BUrger Blaster, or Bugs).
But I would have to say my favorite of my chosen period would be the whole 1987-1996 era. The Secret of Monkey Island - one of my most prized possessions is the actual copy of that game my sister bought when I was 9, the 720K 1990 VGA release - was where I cut my teeth on the PC as a gaming platform in any real seriously big way. I mean, here was a game where you could freely walk around anywhere, talk to anyone, grab anything that's literally not nailed down pretty much, and the portraits of people and creatures were photorealistic as I had the 256 color vGA version. I mean, to my 9 year old mind, this beat ANYTHING NIntendo, Atari, Sega, or anyone else had come up with. And on top of it, it was nice to finally play something that you dont' need to feel stressed out to play.
And through my siblings and their boyfriends......I got exposure to Freddy Pharkas, Monkey Island 2, my first actual DOS game was Ultima 6 in 1993 - I spent my 11th birthday week playing that while out of school with pinkeye, listening to A-ha's Hunting High and Low Album for a soundtrack. I still to this day alternate between the OPL and "A-ha Soundtrack" for that game. My friend down the street had a Mac iwth Sim City 2000 on it - listening to the Bee Gees while playing that. My other friend had his dad's Compaq Deskpro 386, and we played Wolfenstein 3D and copies of the Champ Arcade ports we downloaded at the Auburn Draughton Library. Up the street was John and Matt whose dad bought a brand new Gateway 2000 486 "mega-tower" with Windows 3.1, and he had Mario is Missing, some kind of crazy isometric house-building game like some kind of early version of The Sims minus the "Sims" part, and of course, one of the Windows Entertainment Packs with Tetris. I think from age 11 onward, I spent at least a few hours every few weekends on some kind of PC surfing the early internet or playing games on one via friends. And when I was not playing, or learning guitar (which was most of the time), I was digging through the big boxes and reading the manuals, wondering about what games like "The Lost Vikings" or "Thexder" or "Ultima VIII: Pagan" were like. I was like a secret "nerd" in a way - nobody knew it, they just knew "guitar" me. My bro-in-law introduced me to Ultima, and X-wing.
Some games I really like from that era came later just as "Abandonware" was becoming a thing - like Doom, Duke Nukem 3d, Destruction Derby, Test Drive 3...I got Tie Fighter in the original box from my other bro-in-law in 05'. Diablo is a hardcore favorite of mine on PC and Power Mac both on and offline, and I still rock that on a 486. Recently I've gotten really into Get Lost, Flying Tigers 1&2, and Hoyle Classic Card games.
That said, there's some later stuff I hold onto, I still like the first three Sims games, Robot Arena 2: design and Destroy has been a long favorite since I bought my copy from Wal-Mart in 2003 for $5. Postal 1 & 2 are other standards for me as well....I even install it on my old 486s, even though it does not play well on that particular processor.
There are days I wish things had just paused around 1995, and stayed that way. I even, in some ways, miss not having to be connected 24/7.....using my 486 es with FreeDOS as a quasi-daily driver from time to time allows me to get as close to that as I possibly can, and live the past I never got to have because I was too poor to have it without being lucky to have the experiences I had through other people.