Yeah, I was a pretty tried and true 1st edition guy. I can nail down a handful of reasons for spending decades NOT trading up to newer edtions:
1) it's what I knew for most of my life.
2) It was easy not having to memorize the DMG. Just proclaim "rule of cool" and wing everything.
3) Who wants to learn a new system?
4) Who wants to buy a bunch more books?
When rejecting 2nd edition back in the day it was easy to just say "its not Gygax." But even then it was more about the 4 points above.
In the 90's it was easy to stick with 1st ed. 90% of my player pools would be friends who wanted to play but had little experience with it. So no rules lawyers or power gamers. They were happy to play and didn't care about system. Those were the salad days. Long, amazing campaigns of a half dozen genres.
Then in the 2000's after some years off I entered a period of years where most of my players were seasoned 1st edition wonks. Here I was forced to be more rules wary, or what passed for rules in 1st ed. Forum folk would argue that it's a sound system. But they are wrong (IMHO). Its a mess. So open to interpretation all it leads to is argy bargy and rules lawyering. So many "damned if you do and damned if you don't" situations. It could get annoying. I mean, all you want to do is present a fun game. That thing right there is not even in the top 3 list of what many 1st edition enthusiasts want out of it.
Dissatisfaction with old school D&D and the people who were the most into the edition lead to me running anything but D&D for around three years. And I was happy for it. Some Metamorphosis Alpha, Cthulhu, Runequest, and even Champions filled my gaming needs.
The group suddenly got an influx in its last year or so, of younger dudes who were 5th edition guys who had zero 1st edition experience. I ran a somewhat short campaign1st ed, using the environs of Tegel Manor. It was some brutal scenarios and a couple characters died, which the newbs were unfamiliar with. Though I think this campaign was some of my best DMing ever, they wanted to play 5th edition. So we decided to give it a go with a more or less noob DM.
I ran a bard. What struck me the most was how pretty much every character class is a magic user of sorts. I found that very odd. A bard casting thunder wave? But there were things I liked, such as the standard stat modifiers. Not having to have the hit tables handy was nice. But I wasn't really sold. In all honesty it may have been the ability of the DM that kept me at arms length, but at any rate I wasn't ready to make the full move to the new edition. Though there were good points for doing so:
1) straight up rules so you have less arguing about them.
2) You don't really need all that many books. The PHB and Monster Manual will do (if you don't have power gamers).
3) there is a far far far far far far far greater player pool if you want to start a group. And they skew 20-40 years young. And, heaven forbid, lotso grrrrls..)
4) you can still run games with an old school feel and mentality. Its still D&D if you think of it as that. D20's. Rangers. Elves. It's D&D as you want it to be, dog.
Along the lines of this post but also as an aside, a couple of years before leaving LA I had a shot at putting a Champions group together with a lot of people who weren't in my regular group. I love running Supers campaigns so I gave it a real go, but my Grognard attitude about edition got in the way. I wanted to use the old Hero 4th edition, the one that was a sort of all inclusive system for all comic book stuff, not just superheroes. I even had multiple copies. But the folk I was looking at running for where insistent at using the newest Champions edition, so I demurred on the whole thing. If I had at least tried to learn a newer edition I'd maybe have had some great games of Champs.
When I moved into my new town the other year, I started an old school rpg meetup and tried to get some 1st edition going. Though the meetup had a lot of folk join it, there just was not that much interest in actually playing it.
So I got involved in a new campaign at *gasp* a game/comic shop. Dungeon Crawl Classics seemed super popular, but I got involved in some D&D after a few fun games of DCC. The 5th edition DM I played under for a few months was a good guy, and a sort of unofficial community leader, but he was inexperienced. Though fairly talented at running from material he did not prepare all that much (the revamped Keep on the Borderlands), for me the lack of prep shined through. Lots (and I mean lots) of reading the text box descriptions out loud. And actual role play was about zero. In one session the other players would be gung ho wanting to kill all humanoids, then the next would have all this sympathy for them and be anti-killing. It was all fairly annoying, though to be fair many of them were more or less noobs. One guy, a young redneck construction worker who showed up covered in drywall dust, was a jackass at a nuclear level. When at some point I asked the DM what a particular statue represented and he replied, annoyed, "it doesn't matter"I knew I was more than ready to get out of the shop and get my own hand picked group going. Something like that should matter to a DM, not to mention a player actually showing some interest. If you are unprepared with the material just make something up that makes sense. You don't have to look at it as art, but put a little work into it.
So I did with the help of a couple I met through the local game shop Facebook page. They actually became my besties in general in town, also getting me involved in a local poker group. I got to do a bunch of great games (centered around that old classic The Lichway, which I'll probably talk about in another post) but then the whole virus thing hit. So I started looking into running games on Roll20, with some helpful remote guidance from the comic shop DM I mentioned above.
OK, its all kind of off topic from the title of this post. Getting back to that I guess my point is a transition to a newer edition was fairly easy. I find it enjoyable because I can inject my old school philosophies, such as they are. Noobs at the shop didn't want to hear about it, and maybe they were right. Stop talking and just run new edition games and find my old school nostalgic joy within what I bring to the table as a DM.
More play injected with my old school style, less reminiscence. Walk the walk.