How to introduce a new player is a tough call. It is relevant to the issue of making 5e into an OSR-style game.
My son never saw live streams to get excited about D&D. He saw live play. Some kids at his school were playing 5e during recess, mini sessions every day. A small crowd hovered to watch, including my boy. He told me about the game and wanted in, but these young players didn’t really know how to play. I had to run games for him or he would think D&D was arena fights with monsters from the Manual. Now he runs D&D for his friends (online during the pandemic).
Initially, I had dug up my crinkled-up Moldvay Basic copy from 1981–my preference if I was arm-twisted into playing D&D. My son looked at me and said, apologetically, “Yeah… the kids in my school will never play this.”
Why not? you ask. First, they’re kids without cash. Parents had already gifted some of them the books they found in Barnes & Noble or on Amazon: 5e books. Then it all comes down to glossy presentation, high production value, cool power-ups per level, per class, and evocative fantasy art in synch with the present times. Only one kid in my son’s gaming group is white (mine is “mixed”), and the uniformly European image of old-time games is subtly off-putting to these kids who want to identify with their heroes but are trapped with us in a racially-charged reality that conditions our imagination. 5e is more in step in its image with the changing demography of the Anglophone world on this front.
In short, it doesn’t matter what the rules of the game are. New kids will play 5e, and today’s kids are tomorrow’s gamers. The more old people tell them “that’s not the real way to play” the more they will ignore them. Imagine, you grognards, that your dad told you, “None of that softie fantasy wizard stuff! This is how to play,” and pulled out some dusty Avalaon Hill tactical wargame. These kids want a chance to be heroes and to have the ability to make a difference, and OSR gamers want them to tap the dungeon pavement with a pole and take a year to get to second level.
The new kids will hack their 5e games with house rules in any case, just as we hacked our rules, because D&D rules have always been dysfunctional (in my opinion). Somebody suggested to me that one reason for the popularity of D&D is that you pretty much have to house-rule it to make it work, because it’s terrible. The idea is that it forces you to think about rules, and get engaged with the game, because they’re so clunky.
The newest players, Middle School boys and girls, are excited by presentation, and that is what they will invest in. The OSR people have a lot of work to do on this front, if they care about new players. Focus on kids’ interests and input, boys and girls, and not on groaning about the times of yore, says I. The “Old-School” label was an embarrassing self-inflicted injury on this niche of the hobby, and polarizing, too.
My suggestion is that you encourage all new players (like your nephew, SunkenPlanets) to play 5e. OSR, I find from experience, is a turn-off for lots of kids, especially when grognards groan about “the way it used to be, the way to do it right.” You already lost the fight when you said we’re OSR, “we’re original” (especially when that’s not true). Kids don’t want original. They don’t want cooler-than-thou posturing. They want fun. Focus on that.
What do I think you should do instead? Let them play 5e but produce “rules streamlining” sets that are OSR-style Trojan Horses. Call it “high-risk adventure” not “old-school.” It should come with a slightly speedier character creation kit, simplified stat blocks for monsters, and more inclusive images. This will get new gamers to play 5e more in the way you like.
I think you’re right that gamers who play 5e will have more friends, too!