Old School, New Players

TL;DR: Start PCs at 3rd level or higher to get them hooked on old school D&D.

What's it called when you're nostalgic for something that came before your time? I have that for TSR-era D&D and its OSR relatives. There's something beautifully simple and flavorful about it and yet I have only really captured the imagination of a couple players over a dozen sessions and one shots of OD&D and B/X. Most find the rules too arcane, the abilities lacking, the progress slow, and most of all it's too deadly.

Let's give the players credit. From a certain perspective all of those are certainly true given their experience. Most of my players are board gamers whom I successfully talked into a 5E campaign. Not a lot of RPG experience. Not to mention while I voraciously consume OSR content, the OSR itself (not even the editions they celebrate) came long before I found the hobby. So if I failed to deliver a compelling world brimming with adventure well then, I can shoulder my share of blame.

Why level 3? For starters, Gygax was rumored to often start players there and I've seen other grognards follow suit. By 3rd level Fighters can whack a few single-HD creatures in a round. Magic Users have more than 1 spell. Clerics actually have spells and can turn low-level undead semi-reliably. The Magic User and Thief are no longer fearfully ducking for cover at every stray goblin arrow or painstakingly probing every inch of dungeon floor. You could start higher, but at 3rd level each class has access to a modicum of their archetypal abilities.

At 3rd level the players can make more choices about dungeon level. Do they want to troll level 1 for easy marks to beat up and steal their milk money? Or test their mettle on level 4 or 5 in the hopes of striking gold?

3rd level still feels plenty dangerous. No, the players didn't "earn" 3rd level but neither do they "earn" 1st level just as nobody "earns" their natural, genetic abilities. Yes, you want players that excitedly roll up their next character when the first goes down in minutes. But you don't want a potentially good player thinking your "gritty realism" tastes more like nihilism.

Does each level add more abilities and therefore more complexity? Sure, a bit. But DMs generally bear the burden of the rules anyway. This is a feature as players are free to figure out both the world and its rules as they play. Not to mention if they don't know the "rules", they're far less capable of arguing them.

Don't we want players looking to the world for answers instead of their character sheet? Yes, reward all manner of creative and resourceful thinking. The players need to experience that the fun and sense of accomplishment comes from being clever in dire circumstances and earning power, not having built a character with the right powers to render the challenge inert. But having one or two versatile tools in the box may actually stimulate more creativity than the desperation of having none.

Make the player's choices matter. Show the world reacting to what they do. How has the environment changed? How do the NPCs treat the PCs differently now that rumor of their deeds has spread? Players should always be making the decision to put themselves in mortal danger or have reasonable chance of escape.

If you don't choose 3rd level, I understand. But avoid starting at 1st level with a table full of players new to old school. They need to see what's achievable in the world so they hunger to earn it. Once they've got some experience (ha!), once they "get it", then they may appreciate the glory of starring in their own rags to riches story. They may enjoy the macabre humor of death lurking a half-pace beyond stupidity.