Old School Essentials Classic Fantasy.
Start here, in our quest to replace 5E once and for all, clearing out our minds from the confused builds, the myriad action types, the 30-minute turns, the required character creation software, the power-gaming, and the needless complexity to push weak builds (compared to B/X and BECMI characters) up to a 50% level of power of the rules we once had. We don't want system lock in and character designers. We want fast play. We want more in-character thinking and planning, and less build-crafting and rule-exploitation outside of the game's world.
OSE allows maximum immersion.
Our goal here is to completely replace the need for 5E at the table, while keeping things on a Shadowdark level of simplicity, while not going the Shadowdark route. We want structured, non-random progression, no torch timers, and a mode of play better suited for both theater-of-the-mind and map-based play. A progression role should not determine character power, or weaken it if nothing good is rolled.
We want a game where we track time in a notebook, not in some sand hourglass or phone timer in the real world. A phone sitting on the table can suddenly ring from a telemarketer, and tracking a timer in the real world takes us outside of the world we are trying to be in. No outside timers gives us the freedom to say "three days pass" and keep the game moving to the next scene. Yes, we can do that in Shadowdark, but I can't pause a live game as easily and play with time as I can in OSE.
Shadowdark fundamentally changes the concept of time in an OSR game, and the classic "check mark tracking" time is one of the central concepts of an OSR game. It is hard to call Shadowdark an OSR game because of how radically it gamifies time tracking, and it keeps phones involved in the game due to the need of a timer (and phones being the most common timer). This is going to be a radical statement to make, and I love Shadowdark, but it is true.
Shadowdark is a great board game played in real time with a group.
OSE is the better role-playing game.
Many people would start with Advanced Fantasy for "more stuff" but don't make that mistake. The Classic tome is all you need, to start. As your game expands, then pull in the options from Advanced. All you need to rebuild is a simple set of basic classes to start. Everything with Advanced is 100% compatible, so don't worry about having to rebuild characters. the only rule from Advanced I would pull in to start is Weapon Proficiency (AFP23), if you want that detail with martial characters. Proficiency rules allow for an extra bit of character power boost, so your fighters may want this rule, so if you want, have a copy of Advanced on hand for later on.
I would start with the Classic Fantasy book. Just those seven classes are our game's "Basic Set" and will serve as our starting game. You need an adventure and nice-sized starting campaign too, but we will get to that. Our best chance of success of completely replacing 5E will be in starting with just the basics, and not watering down combat power with too many odd and specialist classes. You start throwing in half-caster and half-martial classes in the mix and those will weaken party strength and require skilled players to make the most of, plus alter the basic play style.
We want our game play to start with "kick down the door, send the thief around back, and start flinging spells" that classic style of play. Throw in an oddball class early, like a bard, druid, ranger, or a merchant, and you lose that smash and grab style.
Also, if you throw in too many races too early, your entire world design becomes muddled and confused. We just want Humans, Dwarves, Elves, and Halflings. We just want those races to start! Special and rare ones can come later, and that will keep them feeling special in the setting. When the Dragonborn show up, they will be from the "Dragonborn kingdom" and the players will want to go there. Keep that option open, and do not play that card yet! Forbid players from creating Dragonborn until the adventure "unlocking the kingdom" is finished, and keep that race option as a "campaign achievement" for finishing a milestone. Do the same for every special race, like Drow, Ratlings, Gnomes, Half-Orcs, Tiefling, and every other character option.
5E sucks. They give you far too much to start, and I have had new players walk away from a pile of infinite garbage choices (that all means nothing) rather than decide between a handful of meaningful choices.
5E is way too "Star Wars Cantina" and takes away any possibility of locking races (and classes) behind campaign achievements. If you want to lock those new classes in the Advanced Fantasy tome behind achievements, do that too! Illusionists. Knights, Paladins, Acrobats, Assassins, Bards, and Rangers should be all tied to some adventure where you encounter them first, and that needs to be completed for players to "unlock them."
Perhaps we create a "circus adventure" that unlocks Bards and Acrobats? That sounds fun! that gives the reason for players to complete it rather than "XP and gold."
See why we started with just the Classic Fantasy book? This gives us control of character generation, and puts all the interesting, specialized, and varied options behind campaign achievements.
And new campaigns start over with Classic Fantasy and expand from there.
Now, you have your base set of rules, with advanced options to add later. Since I like the D&D 4E flavor, we will need the Carcass Crawler Zines, especially Issue 3 with the Dragonborn and Tiefling. All of these books are more than worth picking up, but don't go overboard adding options from them just yet. Issue One has combat talents for fighters, another handy resource to have. I know I said not to add anything, but we are planning a game, and that means making a map to know where we will go without wasting our time on books and different routes that will waste our time or lead us astray. Plus this gives us more potential "unlocks" for our campaign achievements.
Note, any OSE book that adds options should be made "unlocks" and this will give you far more control over your game and give players new things to shoot for. Plus, if you feel an option would break the game or mess up your world, do not include it!
Campaign unlocks also make character death sting less. Perhaps once Bards were unlocked, our Thief character who died in a 80' spike-filled pit trap may be allowed to pass on to the Hero's Realm and that player may want to roll a Bard next.
Starting with Classic Fantasy gives you that control and drives motivation, do not give it up by letting "everyone have everything" to start.
Okay a few special mentions that will kick up our game into a 5E-level of character customization. Get the small hardcover On Downtime and Demesnes (ODaD) book. This book dramatically expands your downtime activities, but it adds a few special systems to the game that will make the OSE "basic characters" seem like fully detailed 5E characters in no time.
This book adds talents, skills, new weapon proficiencies, and expert/mastery trainings. We get item (normal and magical) item crafting, potion brewing, spell research, library creation, and many more rules. We also get rules for downtime ability score improvements.
Talents can train "feat like" abilities that you can make up yourself, such as "shoot into melee" or "dark fighting." Skills add a whole new system that uses the OSE ability check system and allows characters to pick up skills for any area outside the OSE rules.
Want your magic user to get crossbow training? You can do that here, but it will cost you. I would use referee discretion here, but it allows for new types of characters and special builds. On the balance, this is a good thing for character customization.
Do you have a favorite character ability in 5E? Discuss it with your referee and come up with a sensible design. Make it a talent. Pay the 3,000gp cost and spend 3 months training it. We're done. We don't have to talk about 5E again, nor pay a VTT to host our characters for the right to choose that ability. And buy the digital books.
What is the balance? All this gets more and expensive as you go higher and higher, and more powerful. There are reasonable caps on all the special training options, and this allows character to have a lot of freedom in training special combat talents, techniques, skills, and other bonuses. this also burns a lot of gold, so it gives the party a reason to get out there and loot the countryside of every gold piece they can find.
With ODaD, you could even have a high-level character spend hundreds of thousands of gold pieces creating a crossbreed or construct with a few special abilities, like a werewolf-vampire with a few of those powers, and then use that as the player's next starting character. Sure, it is OP, but this is B/X, dying is trivially simple, and you are welcome to set that as a campaign goal for your magic user.
This is OSE! Not 5E! Players CAN do that here!
Break your preconceptions, please. There is a world of better games out here that free your mind.
On Downtime and Demesnes will dramatically change how you see OSE, and it will begin to allow characters to have a high degree of customization and specialization, and it will take your game beyond 5E's overly simple level-based progression, and link progression to downtime and gold, rooting your campaign stronger in the world, and forcing players to engage with it to find that wealth to "buy all this cool stuff."
With 5E, you could sit there and "ride the table" all the way to level 20, and get everything you need except for a few magic items. Why engage with the world and get gold? My class progression table, multi-classing, and subclass choices will take care of it all. 5E's video-game-like progression that automatically gives you "free stuff" is a fatal flaw of the system.
OSE keeps characters hungry.
ODaD transforms the game and opens the system up to player input and specialization that they will love taking advantage of. This is what people think "5E has" but it really doesn't, when you realize the powers you get are "programmed into" progression tables and allow for far less options and specialization than ODaD gives you withe a simple, small, concise, but incredibly powerful book.
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