Not being able to send settlers to occupied outposts
TLDR: Although it would be nice to have the flexibility to send settlers to outposts, I don't feel like it would be immersive or balanced to simply lift that restriction entirely without implementing a more complex system with limits. Otherwise, the current system where we can send slaves to outposts is the better option.
Sorry if this is in the wrong section, the following is less about fixing issues with Conqueror, and more just a random idea I was having for the mod.
At first it bothered me that you can't send regular settlers to outposts. However, you can send slaves there. I typically send 1-2 slaves to each outpost to work an essential industrial plot or two. I don't think it would be immersive to be able to send a bunch of "square" citizens to a raider outpost and expect them to play nice.
Picture this: You fast travel to your Outpost at Zimonja and walk up the hill into the settlement. There you find 10 or so raider soldiers of various rank, stationed at martial plots and hanging at recreational plots. You have one captive working a power/industrial plot. Then, you walk into a dusty post-apocalyptic bar to buy a couple Gwinnett Stouts and some Psycho from an NPC named "Raider Affiliate".
I think the only immersive and balanced way to send settlers to outposts would be to add another settler type, like "faction ally". A citizen settler who is not a "made" member of the gang, but who is more trusted by the gang and feels at home in an outpost, and can therefore work the same plot types that a regular settler can work in a vassal.
Here's a potential mechanic for that:
Only allow 1 or 2 settlers max into an outpost (based on a ratio thing, like 1 settler per 7 soldiers?), with a BIG production penalty at first, maybe the same as when you change a soldier to a "worker". Over significant time, when the settler/citizen has spent enough game days (weeks?) in an outpost, the settler can "rank up" to "faction ally" ("raider affiliate", "minuteman sympathizer", etc.).
Once a "faction ally", the settler now produces as much as a happy settler would produce in a vassal. Let them work any plot in an outpost besides a martial plot (now outposts can have bars on commercial plots!). For "ranked up" settlers, take away the ratio restriction, so that when you take a new outpost, you can send 2-3 of your "faction allies" in to boost production and build up the new place. Allow them to be moved freely between outposts/Vassals (for this reason they would need a special category in "soldier tracking" for the map, and in the settlement reports at the war desk). You can even make it so that if placed in Vassals, they boost morale so that less control is required.
But- don't make it easy to rank them up. Just like a citizen getting in closer with some mobsters, it should take a while before trust is built on both sides. Regular citizens DON'T WANT to hang around criminals because they're scared. Before the settler is ranked up, there can be a probability (based on the happiness/morale of the outpost?) that the settler will either run away or even get killed by one of your soldiers (imagine some petty dispute about "respect" lol). In other words, you can send a settler to an outpost if there are at least 7 soldiers, but if happiness/morale is lower than 80%, you're taking your chances! For average game play, if you start out with a settler in your first outpost, that settler shouldn't rank up to "ally" before you get your first rank 3 soldier or so. The mechanics should be set up so that for average game play, as the campaign progresses, you have no more than 1 "faction ally" per 10 or so soldiers. This way, outposts will always be distinct from vassals, and any unbalanced "loophole" where you can just spam outposts with settlers is avoided.
All of this was me just spit balling. The above would probably be a ton of work to implement, and there are probably bigger priorities, and undoubtedly cooler ideas out there. Even though at first it was a little confusing and frustrating, I have grown to like how it works where besides soldiers, only captives are allowed in outposts. I can only think of two issues with the current (old) Conqueror "no settlers in outposts" thing:
1) If I enslave a settlement to make a new outpost, then I get a bunch of slaves. Maybe I just want one or two. So, I have been only starting with one "take captives" attack, until I have taken enough outposts to use all of those slaves... Then, if I want to take captives in another raid, I get a large number of slaves again. I have tried just slipping a slave collar on a random settler and sending them to an outpost, but when I have tried to assign them to a plot, I get an error message about not being able to assign the plot to a "non-settlement NPC". (Maybe this was a unique NPC and I didn't know it?)
2) (Not important) I would like the aesthetic of having somewhere alcohol-specific in the outpost. It would feel immersive to have a crusty biker-esque bar in my raider outpost, but currently (since captives can't work commercial plots) I would have to change a warrior to worker mode, and soldiers aren't bartenders. Being able to send in at least one settler per outpost could be one solution to this. So would lifting the restriction on captives working commercial plots in outposts.