To briefly summarize that post, my B1 sandbox contains the following locations:
- 01.05 Zerelda's Camp: A temporary camp for a party of high level adventurers who are looking to build a stronghold.
- 02.02 Timbershore: A large town ruled by an evil high level wizard and an evil high level cleric.
- 02.05 Giant Eagle Nest: The lair of a flock of giant eagles.
- 03.01 Fayette's Hold: A high level fighter's castle, now occupied by brigands.
- 03.02 Ebongrove: A humble thorp, terrorized and occupied by the brigands of Fayette's Hold.
- 03.04 Okorg's Den: The lair of a band of ogres.
- 03.05 Quasqueton: The dungeon which itself is the subject of Dungeon Module B1.
- 04.03 Owlbear Den: The lair of a pack of owlbears.
- 04.04 Jinglepuff's Burrow: The lair of a tricksy leprechaun.
I already have perfectly adequate sketches of each of these locations. I know who are the adventurers that make up Zerelda's Company, who rules Timbershore, who the brigands' leader is, how many giant eagles and owlbears there are, what the ogres want, what Quasqueton is like, and what Jinglepuff gets up to. I know that the evil wizard is plotting against the adventurers, that he was once aligned with the brigands but now desires to be rid of them, and that he is courting the ogres. I know that the ogres are pissed at the townspeople because they suspect them of stealing their treasure (when really Jinglepuff is responsible).
That's all gameable, and a DM who's comfortable with improvisation can probably make a little bit of detail go a long way. But the benefit of having a sandbox of this size is that you can go really detailed and still probably have most or all of the material fully prepped before or shortly after starting to run it. As of this writing, I have one and a half important locations within Timbershore left to detail. Everything else is pretty much done, and we're only a few sessions in.
But where do you start? Surely, Jinglepuff's Burrow, buried and secreted away deep in the woods, is not as important as the starting town or the dungeon. If I prepped all the monster lairs first, then showed up to the first session with only those ready for play, we wouldn't have much to work with. Surely there's some order of operations to follow. Where to begin...
Fortunately, I have a blog post which points the way. Here, I take a deep dive into settlements, strongholds, ruins, and monster lairs, describing each location type's gameplay feel and purpose. I also place each on a complexity/player agency gradient. Less complex location types like small settlements and dungeons offer the players a great deal of agency even at low levels, while more complex location types offer little agency until the characters accumulate the power and resources to deal with them as they wish.
At 1st level, the players have more agency in the dungeon than they do in the 20th level wizard's stronghold. They can go to either place and poke around if they wish, but their lack of power and resources will limit the extent to which they can do so. They can go most places in the dungeon with the proper use of tactics and spells, but in the wizard's stronghold they might be limited to an audience with one of his henchmen in the receiving chamber, whereas at high levels they might be able to use their superior abilities to teleport directly into the wizard's inner sanctum to confront him.
To summarize, the final gradient I ended up with looks like this (from least complex to most complex): dungeons/simple settlements (thorps, hamlets, and villages) > simple monster lairs (where monsters are unintelligent/unorganized or very few in number) > moderate complexity settlements (towns)/moderate complexity monster lairs (where monsters are intelligent/faction-like but not huge in number)/strongholds > complex monster lairs (where monsters are intelligent, organized, and vast in numbers) > complex settlements (cities).
Looking at my B1 sandbox, the order of operations might be: Ebongrove/Quasqueton > Giant Eagle Nest/Owlbear Den/Jinglepuff's Burrow > Zerelda's Camp/Timbershore/Fayette's Hold/Okorg's Den. We do not have any complex monster lairs (this would be something like the lair of 300 orcs) or complex settlements (like a city), although we will see that Timbershore is plenty complex on its own.
This makes enough sense. Quasqueton should certainly be the first place I detail (and much of the work is done for me already), and Ebongrove should be simple enough. However, there is a wrinkle - the road into the region leads directly to Timbershore. This will likely be the first place the characters visit (unless, for some reason, they decide to navigate around it) and will probably be their base of operations. That should be a priority as well.
The town will prove to be plenty complex, however, and I will not need all of it fleshed out to navigate the party's first visit. In fact, I'll end up detailing the town in a series of passes, starting first with broad, important details, then drilling down into specific locations within the town, once again according to our complexity/agency gradient. It will be important to know the general layout of the town and where certain services can be procured immediately, but the thieves' dens, ruined mansions, and haunted tombs can wait, as can the strongholds where high level NPCs live.
Instead, my order of operations might look more like this: Timbershore (first pass - districts and broad details) > Quasqueton > Ebongrove > Timbershore (second pass - keyed locations and monster lairs) > Giant Eagle Nest/Owlbear Den/Jinglepuff's Burrow > Zerelda's Camp/Fayette's Hold/Okorg's Den > Timbershore (final pass - high level NPC strongholds).
Your order of operations may vary. If the characters enter the region in a hamlet before reaching the town beyond, you will start with the hamlet. If there is a monster lair blocking the way to the dungeon, you'll want to detail that before the dungeon. You should identify locations that your players will definitely encounter first, then anticipate those locations they are likely to want to investigate early.
Looking at my map, I might be more flexible with my order of operations. Timbershore and Quasqueton will still be first, followed by Ebongrove, but after those, I might want to mix things up and take a look at Zerelda's Camp, Fayette's Hold, and Okorg's Den (due to their proximity to inhabited lands). The Giant Eagle Nest, Owlbear Den, and Jingelpuff's Burrow can come later because they're more remote. Or, because they're relatively simple and easy to detail, I might wish to knock them out early. I might want to jump around for more variety, or simply maintain momentum by focusing on whatever seems interesting to me at any given time.
Just as I created minimalist sketches for every location before detailing any of them, I might do a "second pass" at each of them before diving in further, just to give me a little more to work with. For example, I might roll up exact numbers of monsters and their treasure and jot down their stats at each location before digging in to actually key them. That's the kind of stuff I definitely don't want to do at the table, but I can probably improvise an owlbear den on the fly if the players zig when I thought they would zag.
Don't panic if you don't have everything prepared by session 1. It doesn't have to be perfect by the time play begins. The intention is to anticipate the players' actions as best you can, but to also give yourself just enough to cover your bases when and if the players do something unexpected. If it goes according to plan, you'll have each location fully realized before it makes contact with the players.
Then, they get to wreck it. That's where the fun is. But you have to build it for them first. Future posts in this series will describe how that's done.

