For me, dos gaming all started a long time back when my dad bought a 386 computer. My first dosgames were Scrabble Deluxe, Crimewave and Xenon2. All these came with the 386. At that time, there were only these games besides the Windows Entertainment Pack (WEP) games that PC sellers like to bundle up with new PC (one CD rom - licensed version of Windows 3.1 and another CD-ROM WEP). Following this, got Alley Cat, Prince of Persia, Lemmings & Oh no more Lemmings, Pushover, The Simpsons & Magic Pockets as well as a CD-ROM of shareware games (include Crystal Cave, Secret Agent, Bio Benance, some kind of interesting game on doing a blood test - though it's a simple shareware but it's quite educational). Most of them my sister bought. Not bad, my sister buys to play the games and I get to enjoy too.

Then I got from school this dos shareware clone of the arcade game, Hexavga. It's a Columns game variant. The Computer teacher was so nice, seeing that we had free time before the class started, she copied the game into our school PCs. I brought a copy home. Anyway, it would have been nice if more teachers were like her.

3 cheers for her. Otherwise, I would have ended up getting bored to death by playing Minesweeper and Solitare while waiting for class to start.
Funny thing is that I had so few dos games than I had Apple II games so sometimes I ended up playing the Apple II games. The dos games graphics look terrific to me at that time after seeing the monochrome Apple II games. It was especially a delight after playing Karatake on Apple II and finding the dos game, Prince of Persia having the same character and produced by the same company and creater and having an even better gameplay. I really treasured the few dos games that were available and enjoyed them. Sadly, I haven't ever completed the dos games except for Crimewave and Prince of Persia. It was an extremely joyful experience completing the game by myself. The rest of the game I couldn't complete because I got stuck and after spending days on them I still could not solve and gave up. At that time, there were no access to walkthroughs or cheats unlike these days it's so accessible cia the internet.
I still remember buying the shareware version of dos game, Brix on a 3 1/2 inch floppy costing $12.90. It's really too high a cost for a shareware game. At that time, I did not have internet access and no CD-ROM drive. Only have a 5 1/4 inch & 3 1/2 inch drives. However, I can truely say that I enjoy finishing all the 112 shareware levels of Brix and solving them all without any help.
Many years later, after upgrading to a Win 95 Pentium with access to internet, I collected a lot more dos games by downloading sharewares & freeware through the internet and buying those 40 to 200 shareware games on one CD-ROM plus a lot more other games. As the collection grew, it became like a hobby similar to collecting stamp. Buy and keep but hardly use.
My dos favourite games, I have kept them and even tested them on each newer PC that I used. When I started working and was given a Pentium III Win 2000 laptop on loan for work, I tested on it too.
Then about 3 years ago when I have this Pentium 4 with Win XP, I tested the old dos games on it too. Happy to say that there are still a few rare dis games that can be perfectly playable on all machines without any emulation such as dosbox needed. For these games, the programming really can stand the test of time.
Too bad I never got to try Win 98 but from what others say about it being better than Win 95, it's not so much of a regret. I liked my Win 95.
Sad to say some very old dos games could not even be played properly even in under dos of 386. Now that there's emulation like dosbox, I should try those games again. One thing I hated about some dos games was that I could find any way to quit the game such that in the end I had to hit Alt-Ctrl-Del to terminate or reboot the PC.

Nowadays, with dos emulation like Dosbox, all one needs to do is close the dosbox window to end the game.
Over the past few years, it was really a delight to find bargains of old dosgames in computer game shops or even bookshops.
What I enjoyed more was finding level editors to old dos games and being able to create some levels myself or playing levels created by others. Too bad not every game had a level editor.
It's also very interesting to see dos version evolve into windows versions for game sequels. So far, I bought all the Lemmings titles and Incredible Mahine titles that ever existed for PC. The are 2 titles where one can see how the graphics, sounds and menu changes over the years from dos to windows.
It is also interesting to find out that games that were available for old PC such as Commodore 64, Apple II, Amiga etc were also available in dos.
Sometimes I wondered whether I would ever complete those dos games that I started on before. In the past I got stuck. Now with walkthroughs, I can continue. However, the problem would now be that I don't have much time, not in the right mood, need to practice to get back the game skill and also need to remember where I got stuck. It's just too tedious to start all over again, knowing that you used to get stuck on level 60 or 70 of a 100 level game.