(Second time I've made that joke today.)
Let me see if I can define this problem more clearly by talking (writing) about it.
The adventure comes in two broad parts.
The first part is a standard semi-sandbox. There is a dangerous and unusual environment, one very powerful faction and a number of less powerful factions, along with 'monsters', some quasi-dungeons and some industrial and 'heist' type challenges.
This isn't much of a problem as standard OSR and D&D techniques of information organisation have proven reasonably effective. Factions, 'monsters' and fluid aspects have proven fluid enough that they can be easily incorporated into random tables. Static objects are still static enough that a map is useful. Most problems are resolvable or addressable either kinetically (violence, stealth, escape) or informationally (negotiation, deception or simple obedience).
The level of player freedom is high, although they are geographically constrained, so they should have maximum utility both in deciding how they address each problem and also in deciding and defining for themselves exactly what counts as a problem.
In this first part, the personhood of NPC's is deliberately muted. The relationship of people to factions matters, exactly which individuals they encounter doesn't matter that much. (Actually PC actions can change the extent to which this is true, but that's not important for the terms of this description). People are replaceable and atomised. In this section most individuals are below, equivalent to or only slightly above the combat potential of an average low-to-mid level PC. So if you meet someone, they should be wary of fighting you and you should be wary of fighting them, at least if there is no obvious advantage in numbers or tactical positioning.
To put all this in normal-person language, I tried some weird shit in the first part of this adventure but nothing was so wierd that I had a big struggle where I had to sit down and have deep thoughts about how information was arranged on a page. There were problems, but the common tools seemed to suffice.
The second part of the adventure is different.
In the second part its not very difficult for PC's to get around. The environment is 'soft', it's not trying to kill you. There is *some* potential for kinetic encounters which must be resolved through violence, maneuvering and stealth, but these possibilities are secondary or even tertiary.
The dominant factor is this part is people, specifically the personalities of NPC's. There are about 30 NPC's. There are arranged in about 13 groupings in which you can reasonably expect to find people together, friendship groups, family groups etc. This was to keep the total amount of page-flipping down to a minimum and the complexity factor of different encounters low, at least initially while players are still working out who the fuck everyone is.
No-one is going to remember the details of one of 30 people if encountered in a purely random way, and it wouldn't make sense anyway for them to be wandering around randomly. But you will probably remember a family or friendship group if you encounter them one-by-one, especially if they are visually, socially, poetically and politically distinct. The same way its easy to remember families in a soap opera.
In the second part, as a deliberate design choice, personality *matters*. There are two major groupings with family groupings within those and personal differences within those. Every individual has a unique personality, history and relationship with every other individual. Everyone has distinct loyalties and desires.
Everyone is *really fucking dangerous*. The average combat capacity of an average relevant NPC is rougly at the level that if a mid-range PC group were to try to mug or gank them, they would probably lose at least half of their members and could possibly suffer a TPK. In addition, unless extremely careful, they would enrage the dominant culture against them, effectively being hunted and killed in short order.
This is a deliberate choice to make sure PC's aren't going to try to murder-hobo the last part of the adventure. OSR design makes personality and character important by making that person and character capable of fucking killing you so you better listen to what they have to say.
The environment is static, with about 18 particular places or buildings, two major terrain elements, (a small river with a lake, some dunes) the rest being parkland of a kind, copses of trees, small rolling hills, paths, enough terrain to make sure you can't see everything at once and to give privacy but essentially it's hard to get really lost.
Currently, my way of creating personalities is with an interlocking family tree (mainly useful for the DM to begin with but PCs and players can learn it, or an NPC might literally draw it out for them), simple interlocking loyalties (this person will respect their parents & protect their children and spouse) with minor variations (this person is cheating on their spouse or their children are illegitimate), and with tables of particular specific desires, behaviour patterns and actions.
The shape of a relationship is meant to be indicated by the layout and results of the tables on a page.
So, lets say you run into one particular married group. These people all appear on a double-page spread. They have individual action tables if you speak to them alone and a group table to show what they are up to if you encounter them as a group.
So this particular marriage is invisibly falling apart and this is meant to be shown in the construction of the tables. Their group activities are laced with passive aggression and invisible stress lines, their individual tables create actions & behaviours that are seperate or even opposed. They are bound together only by their primary loyalties to family and clan.
On this other hand, this friendship group between apparently different people is very strong, so if you encounter them together then they are engaged on some exciting and interesting action and if you encounter them alone then their tables naturally turn their intentions and behaviours back towards mutual interest.
In addition to this there is an *evil* faction that entered this area at the same time as the PC's. They are physically weak compared to the main NPC's, but they hate the culture of the main NPC's and want to use deceit and cunning to force it to self-destruct. You can think of them as ultimate shit-stirrers or a faction of Iagos. They have their own plan to fuck everything up and, as the only other free agents in the area, the only people who stand a chance of stopping them are the PC's, should they wish to do that. Its OSR so they could just as easily work for them.
The adventure is intended to run with you kind of socially chasing/being chased by these baddies, with them fucking stuff up everywhere they go and you trying to un-fuck it, and to expose them.
And in addition to THAT, there is also a BIG. EVENT. that everyone is working up to, and how that goes and if and when it falls apart will have a seismic effect on everything.
My problem here is how to arrange the information.
I've got these places, and they are all distinct, but its part of the logic of the this section that place is not very important. There is much, much more information attached to person rather than place. The rules are written so the castles and palaces literally dim and become ashen when their occupants are not there.
So currently, the places stay in place and when you get to one you roll to see what group is there, then you interact with them, and maybe they ask you to do something or you decide you need to do something else, then you move on.
And that's two flips. One, start at the map page "What path do you want to take?", then you move to the place page, then you roll to see who is there, then you go to that page and you roll to see what they are up to.
It's too many flips and it's too disconnected.
Other option is link the people to particular places, at least for the first part, until players work out who most people are and what't going on. But that doesn't feel quite right either.
There's the option of a kind of informational flow diagram that could on the page opposite the area map when you open the book. With that I could build in you meeting people in a reasonable sequence and also include a time factor. Could also include the 'enemy path' so if they arrive somewhere before you then they have the chance to poison the well.
Or could just dissolve physical space, make it fluid, make the person groupings 'solid' and have building rolled for randomly.
Ehhhh I don't know. Anny suggestions? Anyone in D&D dealt with this before?