The play-through (turns 1 through 40):

The starting position
Turn 1: Boss Smiley gets a great starting location on the second roll. There's a river, a forest and an iron deposit nearby, and wild grain a few tiles out of the way. No monsters in sight until he moves to the place I chose for settling, but once he does, I see a wolf lair and a bandit camp. Slim pickings, but the trip also reveals an Air shard and twilight bees in the distance, which is nice.
I settle the city, set the research to Civics, drop the taxes down to none, and cast "Enchanted Hammers". The first building will be the workshop, and the completion estimate is 8 turns. By habit, I also start building the Iron mine, which I should not have done.
Turn 2: I cast "Stone skin" and "Regeneration", Boss Smiley kills the wolves.
Turn 3: Smiley destroys the wolf lair. No loot. He heads towards the bandits, and notices Badra waiting to be recruited.
Turn 4: Smiley beats up the bandits, and sends them to Stronghold. He gets "Potential I" for level 2.
Turn 5: Smiley loots some pork from the bandit camp, then finds a Dragon cloak in the carts of an abandoned caravan. He notices some misplaced wares, and a dark crevace guarded by a rock spiderling.
Turn 6: Badra wants 220 Gildars to join, which I do not have.
Boss Smiley loots the misplaced wares, and find a fire resistance potion. It will come handy, because the move reveals an Ignys near an Earth shard and a patch of wild grain. Unfortunately, there's also a stalker nearby, and Boss Smiley cannot handle it without more luck than I would count on. I also notice a Water shard near the spiderling. Next to the shard camps Arando's army, which is also very much out of Smiley's league.
Turn 7: Smiley kills the spiderling. I cast an Arcane Monolith, start building a Water shrine. There's iron ore in the Monolith range, but I'd rather save the Guildars for later.
Turn 8: The spider lair yields a leather cuirass.
Turn 9: Right on schedule, the workshop is completed. I start building a lumber mill. Smiley kills a darkling lurker, which takes him near the Ignis.
Turn 10: The Ignys heads toward Smiley. The darkling camp yields a leather helmet. I notice a group of Knights of Asok near a prestigious location. I am not sure Smiley can take them on. I hope they do not chase him.
I also discover the lair of the Ignys and Csilla's camp. Another Empire hero Smiley cannot hope to defeat.
Turn 11: The Ignys attacks, and thanks to the Dragon cloak, Smiley defeats him handily. I'm saving the potion for the fight over the lair. Smiley gets "Quick" for level 3. I send Smiley toward the Earth shard. An abandoned caravan and well guarded by a butcherman come into view.

A good place to get some loot and experience
Turn 12: Smiley loots the caravan, but all he finds is some pork. On the other hand, the move reveals a great many things. Two stalkers with their lair, two bandit armies, a humble inn, a water shard, and an Empire hero that Smiley can probably beat. I just hope that no sovereign gets there before mine.
Turn 13: One stalker and the bandits head Smiley's way. Smiley kills the butcherman, and finds a sharp dagger in the well.
Turn 14: The stalker and the bandits charge, and lose. Unfortunately, it seems slaves captured while Smiles is defending are lost, just like all other loot. The experience is all there though, and Smiles chooses the path of the warrior on level 4. Next Smiley heads to the inn, fashioning a stone mace from a decrepit statue he finds on the way. Near the inn, he notices another Earth shard and a bloody clearing inhabited by an ogre.
Turn 15: The research on "Civics" is complete, the growth rate of Stronghold increases, and I switch research to "Agriculture". Of course, "Knowledge" is the immediate target. In the inn, Smiles is asked to clear some rats in return for a Doom club. The rats are close by, and he clears them without trouble.
Turn 16: The Water shrine at the Arcane Monolith is complete. The Slavers' mana intake quadruples... from one. Instead of heading straight to the inn, Smiles captures 5 brigands from their camp and sends them to the city. In their camp, he find a wolf shaped token.
Turn 17: Stronghold reaches level 2 - the newest recruits must be better builders than bandits. Ever the blackguard, Boss Smiley chooses the gallows from the designs presented to him.
Back at the inn, he declines the promised club, and takes 300 Gildar instead. He then dispatches a nearby stalker, and uses the token to summon a wolf. After renaming her "Labor Disputes", and attaching a pouch of gold to her neck, he commands her to find Badra.
Turn 18: The lumber mill is completed, way ahead of schedule. Meanwhile, Turim Mafaru claims that he is too good to be a Kingdom faction's champion, so Boss Smiley takes his spear, hands him a shovel, and sends him to Stronghold.
With such hiring practices, it's no wonder Stronghold is quickly running out of food. Because of this, but also because there's an air shrine across the river, Stronghold begins the construction of river docks.
Turn 19: Labor proves to be a great runner and quickly reaches Badra. Badra must approve of the pouch's contents, because she joins the Slavers' cause. Immediately, the two ladies split up and start exploring.
As for Smiley, after dispatching the banished ogre, he creates another ancient monolith that allows the exploitation of two shards and a patch of wild grain. Unfortunately, the monolith reveals a nearby squad of Asok knights. Rather than risk losing the mana investment, Smiley trades his dagger for Mafaru's spear, and goes knight hunting. On the way, he notices an Air elemental's sanctum.
Turn 20: Smiley notices that his mana is so low he could not even cast "Haste" against the knights, so he takes the long way towards them. While doing so, he spots a life shard, some wild game, a troll and another Empire hero. Where are Kingdom heroes when you have 300 Gildars burning a hole in your purse?

If not for some old, old pork... this fight could have ended quite badly
Turn 21: The knights actually head away from Boss Smiley, so he attacks the air elemental instead. The battle does not go as well as earlier ones. Smiley uses up the mana he was saving for the knights casting "Haste", and still, after a few blows are exchanged, both combatants are near death. Fortunately, Smiley has pork in his backpack, and somehow manages to gulp it down while dodging the elemental's pike. This makes all
the difference, and Smiley is the one to walk away.
Smiley gets "Crushing Blow" for level 5. Clearly he learns more than that, because he decides that the knights should probably be left alone for now.
Meanwhile, Labor Disputes discovers a whole menagerie of monsters much too close to Stronghold: wolves, bandits, water shrills, and even a Fire elemental's army. Badra turns around and heads back to Labor. The plan is for the two to team up and dispatch at least the wolves and bandits, if not the shrills.
Turn 22,23: Boss Smiley leaves the knights be, and heads for the troll. Badra and Labor join up, kill some wolves, and head toward the bandits' lair.
Turn 24: Research moves to "Agriculture".
Smiley kills the troll, and retrieves a shield of the Wind from his campfire.
Stronghold stops growing for lack of food. After a brief consideration I decide to spend 102 Gildars on rushing the docks. The next construction project is the sage, because I really need to research "Agriculture" as soon as possible.
Turn 25: An Air shard is brought into Stronghold's sphere of influence, and I start constructing a shrine.
Smiley continues exploring, discovering a widow lair and yet another high level Empire hero.
Badra and Labor come upon a bandit camp and persuade its five inhabitants to join Stronghold's workforce. During the negotiations, Labor is badly injured, but I decide to save the mana for another monolith. Badra gets "Potential II" for level 2. The girls can take a break from fighting, as long as they stay there to keep the scum away from Stronghold.
Turn 26: Smiley finds a Darking cloak in the widow lair. He notices iron and crystal deposits in the vincinity.
Before the girls can loot the camp they just cleared, a bandit and his dog move in. Labor is still hurt, but she can hang back as the bandit is no archer. Once he's sent to Stronghold, the girls finally loot the camp and find another token of the Wolf. Labor Disputes gets a friend - Conflict Management.
Keeping with the canine theme, there's a wild warg pack nearby.
Turn 27: I create another monolith near a Life shard. There are wild wargs and some game nearby, but the Slavers do not know how to exploit those yet.
Boss Smiley keeps walking northwest, discovering a cave bear and a lair of water shrills.
The girls loot an equipment cache, and find an enchanted chain coif. Unfortunately, Badra's not skilled enough to figure how to put it on.
Turn 28: Stronghold runs out of food, again. Fortunately, a sage moves in one turn early, so agriculture is only an year and a half away.
Badra's wolfpack retrieves a leather helmet from a darkling camp.
Smiley destroys a lair of water shrills surprisingly easily, which gives Badra enough courage to head towards a water shrills' lair herself.
Turn 29: Boss Smiley finds a pair of Longstrider boots in the water shrills' camp he cleared last turn. Awesome. I wonder whether Badra will be as lucky.
Turn 30: Smiley kills an ogre, and discovers a Water shard near a prestigious location. I create a monolith that surveys both without exploring the surrounding area. The gamble may not pay off, as two spider lairs turn out to be in the monolith range.

Badra and her wolves
Turn 31: Stronghold finishes building a tower of dominion, and starts working on a set of gallows.
One of the spiders disrupts the construction of the water shrine. 10 Gildars wasted, but it would have been worse if the black widow had gone for the monolith. As it is, Smiley slaughters her, and restarts the shrine construction.
Badra loots a champion spear from an equipment cache, then attacks the water shrills. Labor and Conflict distinguish themselves. Quick runners with deadly bites are nothing to sneer at. Barda get "Potential III" for level 3.
Turn 32: Boss Smiley kills the last spider threatening the new monolith. Now he can loot the spider dens at his leisure.
Badra finds a pair of leather vambraces in the water shrills' lair. Except for the Fire elemental and his army, this region has been pacified, so the girls head to the North which is still largely unexplored.

Aggressive use of an Arcane Monolith
Turn 33: Smiley finds a venomous short sword in one of the spider lairs. Before he turns around to loot the other lair, he notices an iron mine. Not one that he ordered built. One displaying the colors of the Empire of Resoln.
War is only a matter of time, and Boss Smiley is a realist. He forgets about looting, and heads straight toward Resoln. On his way there, he notices a Pariden outpost.
Perfect. A slightly weaker potential ally and an evenly matched enemy. I immediately sign a non-aggression pact with the Kingdom, and don't even bother contacting the Empire. I create an Arcane Monolith, pushing the border back, and laying claim to the mine that brought Smiley this way.
I take a minute to study the Empire of Resoln. Oracle Ceresa is an unstable manipulator who rules 154 wraiths and two cities. They have secured an Earth shard and a source of metal. They do not look particularly impressive, so I fully intend to attack as soon as I stockpile mana for combat and food for future slaves.
Turn 34: A troll demolishes the iron mine at the border of the three nations. Smiley demolishes the troll and gets "Air Disciple" for level 6. In the troll lair, he finds a band of the berserker, but chooses not to equip it. While looting the lair, he notices the Resoln village of Blackstead, population 39.
Meanwhile, research on "Agriculture" has finished, and Stronghold resumes growing. Hopefully, the slaves will never work hungry again. I switch the research to "Mining", with an eye on "Craftsmanship".
The Asok knights that Smiley saw earlier are back. They are moving dangerously close to one of my shrines. I hope that they will leave on their own, and allow Badra's wolf-pack to keep exploring.
The girls dispatch a bear cub, and Badra chooses the path of the Assassin at level 4.
Turn 35: Queen Procipinee has not been keeping her territories clear of monsters and enemy heroes. Boss Smiley kills an Ingys and a bear, then confiscates Klavarra's dagger and sends her to toil in Stronghold.
Badra picks some healing herbs near the bear den, and continues to explore to the North. She notices a Fire elemental's army guarding yet another Caldera.
I cast "Inspiration" on Stronghold, something I should have done as soon as I started my first shrine, but somehow forgot about until now.
Turn 36: Boss Smiley continues to act neighborly and kills a cave bear on Pariden territory. The lair itself is on Resoln lands. Nevertheless, Smiley heads that way.
Badra finds a golden belt amongst some monster bones.
Turn 37: Out of the blue, I receive a message from Lena the Young, leader of Capitar. No one likes being the one scouted, but at least, they appear weaker than the Slavers. I sign an non-aggression pact with them, and trade some magical research. Unfortunately, I see no indication that Boss Smiley's diplomatic skills have gotten us a better deal.
As he loots another band of the berserker from the cave bear den, he spots a refugee camp inside Resoln territory and heads that way.

Some people use breadcrumbs to mark their path. Boss Smiley prefers mana shrines.
Turn 38: Boss Smiley loots a weathered shield from yet another bear den, and kills yet another troll. While doing so, he spots the Capitar scouts that brought Lena's message. They appear to have come from beyond Resoln, which means there may not be anyone to Stronghold's North.
The bad news is, Pariden is sending pioneers into my lands.
The good news is, I have the mana to create an Arcane monolith where I see arable soil.
The bad news is, this only reveals more arable land further east.
The good news is, all these monoliths have pushed Resoln's influence back, and I get another Earth shrine. My mana income is nearing the point where I will be able to create monoliths faster than Pariden can bring pioneers in.
The bad news is, I remember that Boss Smiley made his way around some scary monsters, but not where exactly the lairs were. I fear my monoliths may end up releasing something I cannot deal with.
Turn 39: Oracle Ceresa finally gets fed up with Boss Smiley wandering her lands, and asks him to leave. He complies, only to immediately turn around to speak with the refugees. They ask him to kill some bandits.
Stronghold finishes building the gallows. To celebrate, I raise taxes. Appropriately enough, there aren't many complaints.
Badra finds another pair of vambraces, then takes down a banished ogre. She discovers the camp of Timok the Blade, but decides that he's too tough to take on right now. Maybe on the way back.
Turn 40: A wandering wolf army approaches one of my monoliths. The Pariden pioneers unerringly swerve toward another patch of arable land as soon as I cover the closest one with monoliths. Two more Pariden pioneers, escorted by a champion, head into my lands. Well, time to build a wall of monoliths that friends cannot cross. As for enemies... Stronghold needs labor!
Boss Smiley enslaves the bandits he was sent to kill. While doing so, he spots Resoln's capital - Hagudst. Looks like a good time for a blitzkrieg.
Badra butchers a butcherman.
Note to readers: I'm changing the format of the play-through. Instead of editing the first post, I will place updates at the end of the thread. Those will be of two kinds: "State of the Stronghold" which gives an overview of what is going on, and a turn by turn play-through that will, I hope, have a few more interesting snapshots. Please let me know how you like the new format.