So, with replaying Pathfinder: Kingmaker and doing the first parts of the barony again, I think I hit on one of (though not the only) major reason why Kingdom Management feels off compared to Crusade Management from Wrath of the Righteous, even if both still have issues.
It lies in how it handles building up your settlements/outposts, where Kingmaker is hands-off and points on the board, while Wrath directly contributes to the gameplay in some form as well as points on the board. In Wrath, you can directly feel the effect of every building, whereas in Kingmaker most buildings just mean solving one less problem of that type to get the points to rank up. And even then, the majority of your stat points in Kingmaker will probably come from solving events, which is the core gameplay loop for Kingdom Management.
For example, below at the top are some basic village buildings in Kingmaker while and then some basic outpost buildings from Wrath.
I included the Bulletin Board from Kingmaker to specifically highlight how restricted helpful-to-gameplay buildings are, as the Bulletin Board is famously restricted to Lawful characters. The majority of Kingmaker's basic buildings are more like the example's Barracks, only putting points on the board, and few at that even accounting for synergies like a Watchtower and a Barracks in one settlement. Non-aligned buildings that contribute to the core gameplay loop are restricted to Towns or Cities, of which you are limited at a 3:1 ratio towns-to-villages, out of 14 regions total. As such, buildings are quite detached from the main gameplay loop of Kingdom Management.
By contrast, in Wrath every building helps the Crusade's army in some form, whether it is providing more Material Points for buildings, increasing the energy supply for your Generals' special abilities, hospitals helping with casualty recovery, more troops available to recruit, and so on. This puts the buildings directly into the Fifth Crusade's gameplay loop.
Being mostly outside of the gameplay loop is, in my opinion, the main failure point for Kingmaker's settlements, especially as they do not loop into the RPG side either unlike the TTRPG rules where quite a few buildings add magical item availability or can ease passage across waterways. If buildings affected advisors solving problems, I think that would make them more tangible to the player and make Kingdom Management feel less random as the d20s roll.
All that said, let me be clear that I am not hating on Owlcat for this, as some of this is the limitation of their medium and the sheer range of what they are covering. Kingmaker's scope of your kingdom is everything from swords and sorcery to culture and community. By necessity of budget and manpower to code, this requires abstraction. Still, I think that with a second pass on buildings the worst of Kingdom Management's issues could have been mitigated.
