I've tried a couple of times in the past to add KS to one of my saves, but my sim was miserable and wanted to die all the time, and it just wasn't worth it. I'm never able to get my sim to play through the pain. (Sometimes I DO want my sim to be miserable and want to die, but not over something like woohoo.)

It seems like I was told that my sim would pretty much always be miserable if his partners had low skill (or Renown? or both?), but how does one go about making that happen? Like, my sim would have to do a LOT of woohooing for some of the challenges and to build his own KS skill and Renown (if I'm understanding things correctly). But surely he isn't responsible for also leveling up the entire population on his own.

So I've been thinking, if I add the KS mod for this save, I could also add the KS skill books. The Moar Interactions mod has all of my inactive sims reading skill books, and I'm not sure it will work for the custom KS books, but maybe?

And I've seen people talk about having your sims give educational lectures. Like, throw a party, remove all the stereos and computers from the lot, whip out the whiteboard, and it's basically a "my first key party"? Or maybe more like one of those "get your groove back" novelty toy parties. Idk.

What does everyone else do? Switch households to level sims up manually? Play a really long lifespan and just hope it happens naturally over time?

Anyhow, I haven't played this sim in ages but I'm moving him to Bridgeport and I figure why not try again, but this time view it as sort of a fun challenge. (Though I could never tolerate THIS much challenge in one of my "real" saves. I make life hard enough on my sims, the only fun thing they ever get to do is woohoo!)

You are describing what I call a bootstrap problem -- that is, not a problem with the way KS works in general but rather a problem getting things started. That's probably not the correct term, but I don't know that we have any professional philosophers or logicians in our ranks here, so it's what I call it.

Anyway, when encountering batches of sims whom I am certain must have woohooed plenty of times in their lives before entering my game, either by way of immigration, addition by me in other ways, or maybe I am playing a connected world for the first time, I usually go around handing out some KS skill levels by way of MC. We can't directly affect the Renown scores that way, as number of woohoos is one of the ingredients together with the various minor and major challenges, but skill level we can reach. It just doesn't seem realistic for all those YAs and older to be at Level 0 just because they hadn't experienced their digital lives with the mod in place yet.

After a generation or so passes, then it's just immigrant sims that I usually have to worry about and perhaps adjust, again as they enter my world. But newly aged up teens (or YAs if one plays with limited or no teen romance) do get to start at Level 0 and have to work their way up slowly just like my actively played sims usually do.

Hmm, I guess it's like how, with premades YA and older, most of them are way underskilled for their ages and presumed life experience (i.e. most of the time they can't even make a sandwich), but later generations progress through skill levels more organically. Sometimes I skill stamp premade children and teens with some basic toddler and child skill points because what, am I supposed to believe they get all the way to high school graduation without learning a single thing? It seems unfair for my actively played children to be the only ones who succeed in town. I want them to grow up with peers who have actual hobbies and interests.

Anyways, yes, KamaSimtra sounds exactly like that. xD

So while I'd hoped there was an easy-but-not-too-cheaty way to help inactives gain skill, the way you explained it makes me feel like using MC makes perfect, non-cheaty sense. So thank you for that! I'll think of it like any other skill and give points to whoever seems like they should have them. That will be kind of fun to assess; I can already tell I'm going to want to willfully subvert some stereotypes just to make things more interesting.

Question: will inactive woohoo help at all with their Renown? Like, I know there's more to it than woohoo, but will it be worth it to put photo booths on community lots, for instance? I really don't want my beloved townie sims to be unhappy and I'd like to help them as much as possible without having to actually play all of them.

Yes, inactives should be gaining notches with woohoos like any other sims. I don't know that more or fewer photo booths among other valid woohoo locations would make too much of a difference, I guess it depends on the distribution of traits and other settings and mods that might be in play. My sense is that if two sims wish to "do it," they will find a way and a place and if they don't then they will find something else to amuse themselves with (kind of realistic, huh).

Glad to know inactive woohoos count toward their Renown. Even if they don't woohoo enough to make a significant difference in their score, it's only fair that they get credit for them.

It's always funny when I find out that something I think is universal...isn't. Like, the photo booth. No matter what else is on the lot, photo booths in my towns are in pretty constant use. Even on my homeworld university lot, which has just about everything a sim could want for entertainment, they are fighting over the photo booth. I keep my woohooer settings fairly mild because it gets boring when your sims do nothing but woohoo, but that photo booth can get it. I guess my townies are just extra adventurous, preferring their woohoo both public AND captured on film. Which, good for them.