My experience with integrating full evil nuka world raider game play with SS. Caveat - don't use city plans much in general, and not at all with raider outposts / vassal settlements, so below is regular SS manual-automation not full on city plan automation.
TLDR - pretty much works like any other regular settler SS, just no farms
1. Vassal vs Outposts - only need 1 vassal settlement to progress the storyline quest, and if setup right, even without IDEK logistics connecting to provisioning network (see below) it can feed entire collection of future raider outposts *(assuming you do the full 8+ outposts to also get that achievement)
Since you can't build anything once regular settlement turned into vassal, I pre-setup The Slog as future bread basket for all raider outposts, ~250+ food production using (12) level-4 farms with misc production bonuses. Feeds itself plus 8+ raider outposts even assuming 20+ settlers/raiders each location.
Build your future vassal settlement as normal SS location, make sure all settlers needed are recruited + plots built and upgraded before turned into vassal. Did not test to see if plots still upgrade after turned into vassal - since SS keeps working it very well might but just in case I waited.
Once turned into vassal, it still works like any regular SS settlement except can't build anything new and you are not considered 'the owner'. Since I used the persuasion method to force settlement into vassal, I left all my turrets and defenses in place - didn't need to remove turrets like other guides suggest - they now work great at still defending the vassal settlement and treat both vassal settlers + raider guards (and me) as friendlies when hostiles get near.
All rec plots, commercial, etc keeps working so my 'vassal' settlement is still super happy at ~100 happiness.
2. Supply lines - I use IDEK logistics so can't comment re: other supply line methods. But IDEK seems ideal because even after settlement is turned into vassal OR raider outpost, IDEK keeps working and connects that vassal/outpost into overall supply line network.
Whether the IDEK logistics plot was built before or after doesn't matter - it will keep working long as someone is assigned to it, and SS treats raiders like settlers and auto assigns them like any other settler. Obviously, for vassals you need to make sure IDEK logistics was built before, but use case goes like this --
2a) vassal - build IDEK logistics plot before turning into vassal, either assign settler manually or let SS auto assign eventually, supply line connected and done. After settlement is turned into vassal, the settler that was assigned still stays as provisioner and nothing changes far as supply line goes (e.g. IDEK options to auto collect caps, misc items, etc keep on working).
2b) outpost - if settlement was brand new that you'd never built before when you acquire as raider outpost, then you just build your raider beacon, get raiders arriving, and either manual assign or let SS auto assign eventually one of raiders to IDEK plot and like above you're done
if settlement was existing one you owned and already had IDEK plot sitting there, then settler that was provisioner is unassigned automatically by SS after you use speech check to verbally force settlers out and acquire settlement as outpost. The For Rent sign goes up and basically entire prior-SS run settlement with all existing plots just sits there empty waiting for your new raiders to arrive, and then SS automatically starts assigning them like any regular settler (eventually - like normal SS, depends on when scripts run)
2c) Raider supply line vs IDEK - technically, you now have 2 supply line networks, the hidden invisible one that connects all raider outposts to each other, plus the IDEK supply line network connecting ALL settlements to each other, including raider vassal + outposts to each other and to regular settlements. E.g. your entire stash of workshop items in every non-raider + raider settlement is now connected.
Because of this, technically other than for progressiing Home Sweet Home storyline that mandates at least (1) vassal settlement converted, you don't need food production from vassal settlement to feed raiders at all. Your overall supply line network via IDEK will do that. (I've read robot provisioners work as well to do this but seems IDEK is far, far superior because of both auto collection, instant and automated setup + conversion of existing provisioners/supply line, redistribution system, etc)
So turns out built my The Slog massive food bread basket for no real reason other than role playing they are the ones feeding my raiders when really it is entire supply network taking care of that. Far as storyline quest, a completely empty zero food production vassal settlement would have done to progress story quest.
3. Raider Happiness - nothing changes far as farms being taboo. Any food production still means 1 food = 1 unhappiness. And with SS plots being so large - a single level 4 farm would mean -20 unhappiness. Like normal raider outposts, doesn't matter if raider or robot works it, the game only cares if food is somehow produced there or not, and if it is, get hit with negative (1) unhappy point per (1) food point produced.
So I built zero food plots, but was able to ignore all the silly (to me) raider lifestyle stuff the regular raider system gives to try and manage happiness. Raider amplifiers, chem dispensers, booze stills, etc - not only far less efficient than upgraded SS rec plots, but completely unnecessary unless you jsut want the look/feed of raider lifestyle.
Me - prefer the look of normal SS builds, so I just built homes, commercial, rec plots, industry, and some misc knick knacks from raider workshop items just so it would obviously be raider outposts vs regular SS. I even dressed the raiders in regular clothes.
Basically, other than farms, I selected plots and just let SS handle all the assigning, building and upgrading plots. The only slight deviation is I built lot less homes because I gave raiders the 8 crappiest locations to build - coastal cottage, murkwater, sommervile, etc. Even using Clean and Simple which gives lot more building room, plus All Settlements Expanded for bigger build borders, those still aren't the best locations.
So for raider outposts I built mostly regular beds with only a few SS home plots here and there. Commercial requirements seemed to still be satisfied between combo of plots and beds, or just all beds, far as # of "homes" count required to allow commercial plus commercial upgrades.
TLDR - pretty much works like any other regular settler SS, just no farms
1. Vassal vs Outposts - only need 1 vassal settlement to progress the storyline quest, and if setup right, even without IDEK logistics connecting to provisioning network (see below) it can feed entire collection of future raider outposts *(assuming you do the full 8+ outposts to also get that achievement)
Since you can't build anything once regular settlement turned into vassal, I pre-setup The Slog as future bread basket for all raider outposts, ~250+ food production using (12) level-4 farms with misc production bonuses. Feeds itself plus 8+ raider outposts even assuming 20+ settlers/raiders each location.
Build your future vassal settlement as normal SS location, make sure all settlers needed are recruited + plots built and upgraded before turned into vassal. Did not test to see if plots still upgrade after turned into vassal - since SS keeps working it very well might but just in case I waited.
Once turned into vassal, it still works like any regular SS settlement except can't build anything new and you are not considered 'the owner'. Since I used the persuasion method to force settlement into vassal, I left all my turrets and defenses in place - didn't need to remove turrets like other guides suggest - they now work great at still defending the vassal settlement and treat both vassal settlers + raider guards (and me) as friendlies when hostiles get near.
All rec plots, commercial, etc keeps working so my 'vassal' settlement is still super happy at ~100 happiness.
2. Supply lines - I use IDEK logistics so can't comment re: other supply line methods. But IDEK seems ideal because even after settlement is turned into vassal OR raider outpost, IDEK keeps working and connects that vassal/outpost into overall supply line network.
Whether the IDEK logistics plot was built before or after doesn't matter - it will keep working long as someone is assigned to it, and SS treats raiders like settlers and auto assigns them like any other settler. Obviously, for vassals you need to make sure IDEK logistics was built before, but use case goes like this --
2a) vassal - build IDEK logistics plot before turning into vassal, either assign settler manually or let SS auto assign eventually, supply line connected and done. After settlement is turned into vassal, the settler that was assigned still stays as provisioner and nothing changes far as supply line goes (e.g. IDEK options to auto collect caps, misc items, etc keep on working).
2b) outpost - if settlement was brand new that you'd never built before when you acquire as raider outpost, then you just build your raider beacon, get raiders arriving, and either manual assign or let SS auto assign eventually one of raiders to IDEK plot and like above you're done
if settlement was existing one you owned and already had IDEK plot sitting there, then settler that was provisioner is unassigned automatically by SS after you use speech check to verbally force settlers out and acquire settlement as outpost. The For Rent sign goes up and basically entire prior-SS run settlement with all existing plots just sits there empty waiting for your new raiders to arrive, and then SS automatically starts assigning them like any regular settler (eventually - like normal SS, depends on when scripts run)
2c) Raider supply line vs IDEK - technically, you now have 2 supply line networks, the hidden invisible one that connects all raider outposts to each other, plus the IDEK supply line network connecting ALL settlements to each other, including raider vassal + outposts to each other and to regular settlements. E.g. your entire stash of workshop items in every non-raider + raider settlement is now connected.
Because of this, technically other than for progressiing Home Sweet Home storyline that mandates at least (1) vassal settlement converted, you don't need food production from vassal settlement to feed raiders at all. Your overall supply line network via IDEK will do that. (I've read robot provisioners work as well to do this but seems IDEK is far, far superior because of both auto collection, instant and automated setup + conversion of existing provisioners/supply line, redistribution system, etc)
So turns out built my The Slog massive food bread basket for no real reason other than role playing they are the ones feeding my raiders when really it is entire supply network taking care of that. Far as storyline quest, a completely empty zero food production vassal settlement would have done to progress story quest.
3. Raider Happiness - nothing changes far as farms being taboo. Any food production still means 1 food = 1 unhappiness. And with SS plots being so large - a single level 4 farm would mean -20 unhappiness. Like normal raider outposts, doesn't matter if raider or robot works it, the game only cares if food is somehow produced there or not, and if it is, get hit with negative (1) unhappy point per (1) food point produced.
So I built zero food plots, but was able to ignore all the silly (to me) raider lifestyle stuff the regular raider system gives to try and manage happiness. Raider amplifiers, chem dispensers, booze stills, etc - not only far less efficient than upgraded SS rec plots, but completely unnecessary unless you jsut want the look/feed of raider lifestyle.
Me - prefer the look of normal SS builds, so I just built homes, commercial, rec plots, industry, and some misc knick knacks from raider workshop items just so it would obviously be raider outposts vs regular SS. I even dressed the raiders in regular clothes.
Basically, other than farms, I selected plots and just let SS handle all the assigning, building and upgrading plots. The only slight deviation is I built lot less homes because I gave raiders the 8 crappiest locations to build - coastal cottage, murkwater, sommervile, etc. Even using Clean and Simple which gives lot more building room, plus All Settlements Expanded for bigger build borders, those still aren't the best locations.
So for raider outposts I built mostly regular beds with only a few SS home plots here and there. Commercial requirements seemed to still be satisfied between combo of plots and beds, or just all beds, far as # of "homes" count required to allow commercial plus commercial upgrades.