1. Re-thinking the map
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You know, I really like the idea of delving into the mechanics of holdings a bit more. Somewhat similar to your idea, I'd like to propose a slightly different take that I'm brainstorming as I write this:
(assume, for the moment, the current system, unless otherwise specified)
Levelling up holdings. Basically, as you develop a holding, with increased buildings, it would grow into a higher tier of holding, with new options. The most rudimentary level of holding would be the unoccupied holding, representing an area that is sparsely populated. This could have a terrain type associated with it (forested, grassland, hilly, mountainous, coastal, desert, for example), which could influence the way that holding can develop (a coastal holding could be an economic powerhouse potentially, and it could hold out against sieges for longer, as well, even if its just a city).
From an unoccupied holding, a 'Tribal Village' could be founded (I'm sure someone will be able to come up with better names for my holdings). This would be analogous to the current tribal holdings, representing small unorganized settlements; the lowest tier of development. It wouldn't be worth too much, but there'd be advantages, such as the ability to migrate. As that tribal village develops, it could upgrade into a 'Permanent Village,' representing the typical small rural settlement that was the basis of most of sedentary civilization throughout history. More defensible, and more economically productive, but no longer able to be abandoned like a tribal village would be.
Now, things get interesting. The next tier of development will be more familiar to us. Similar to how the tribal holdings of Charlemagne can develop into either a city or a castle, permanent villages could develop into either a 'Town' 'Minor Castle' or 'Cathedral' (obviously, there will need to be some religious and/or cultural localization as appropriate). These will be similar to CK2's current holdings, so no more needs be said about them.
Except, of course, that that they can level up into even better versions: 'City' 'Major Castle' and 'Basilica' respectively. The utmost level of development for the respective holding type, and representing the pinnacle of civilization.
All well and good, you might say, but what about the odd-man out? The Trading Post? Never fear, they're still around, and better than ever! Rather than just having the potential of one trading post per coastal county, each holding, regardless of type, will have the possibility to have a 'Minor Holding' (or support holding, or whatever you want to call it). Remember the brigade system from HoI3, where you could attach a specialist brigade to a division? Think of this system as comparable to that, where each holding can be specialized beyond its normal 'burgher, noble, clergy' development. They can be developed either by the ruler of a particular holding, or by another character, as appropriate.
Some basic general ideas I have for minor holdings:
Any standard holding will need some sort of 'Minor Holding' to progress to the next tier.
Minor holdings might be restricted by terrain.
Minor holdings might be governed by someone other than the ruler of the holding to which they're attached.
What sort of minor holdings might there be? Glad you asked.
Tribal Villages:
- Missions. Missionaries have sought out your small tribal settlement and hope to convert your people to their faith. Economic and diplomatic benefits abound, but you're likely tying your destiny to that religion.
- Hunting Ranges. Hunting will help feed your people and give you a steady supply of skilled archers and other warriors.
- Pastures. If you want to be a nomadic warlord, you're going to need somewhere to put your vast herds.
- Caravan Post. Sure, you could make a living off attacking those soft merchants, but you could also reap the benefits from letting them pass through your lands unharmed.
- Tribal Shrine. Forget that nonsense the missionaries are spouting. This land is sacred to <insert your generic sky god here> and your co-religionists flock to pay their respects. Why would you want to discourage them?
(possibly, those tribal minor holdings might get absorbed into the main holding when it upgrades)
Permanent Villages:
- Manor. Your local lord has to live somewhere.
- Fortress. This site is a key part of the defense of the realm at large.
- Parish. Your people are longing for a place to worship, all of their own.
- Local Shrine. A local saint's brother's favorite hunting dog died here after choking on a chicken bone. Here come the pilgrims!
- Trade Post. The merchants in the region have come to rely on your village as the premiere spot in the region to sleep without being robbed.
- Cottage Industry. Your village is a key player in the production of uncomfortable brown textiles.
(as you may have guessed, Manors and Fortresses will start you down the path to a Castle, Parishes and Shrines to Cathedrals, and Posts and Cottages towards Towns)
Final Two Tiers of Holdings:
- Port. Situated near the coast, your holding has a wonderful harbor, and the local merchants are taking full advantage of that.
- Citadel. The existing defenses of your holding are not adequate. A proper citadel will solve that.
- Monastery. A monastic order has decided to build their next chapter near your holding.
- Regional Shrine. A genuine miracle occurred right on the spot where your holding's patron saint was brutally martyred.
- Manufacturing Center. Looms? Check. Waterwheels? Check. Canals? Check. Your holding is a focal point of the medieval industrial revolution.
Specialized Minor holdings (will be very restricted):
- Royal Hunting Lodge. The King prefers to hunt here above anywhere else in the realm.
- Major Holy Site. You know, Jerusalem, Rome, Constantinople, Mecca, Medina, these are the places that people will travel to from the other side of the world if need be.
I'm sure I could come up with more, but I think thats more than enough for now.