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(And possible 3) Roxy and Rose weren't living in a place that looked anything like this house, and what I saw of the landscape doesn't suggest that they could feasibly live anywhere nearby.)
HIVESWAP XEFROS X JOEY FULL
Worst case.worst case has potential to go really dark, considering that 1) the house is full of weapons and also doesn't look like anyone's keeping an eye on things like household maintenance (the kids are living off of takeout and there's a mess of books and broken shelving that the dog caused three years ago the house hasn't quite passed the point where it feels like it's one step away from being appropriate to a horror game, with the exception of the kitchen, but it's getting there), and 2) the kids are being menaced by monsters.
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I mean, best case is going to be that someone realized that they only had a functional alcoholic babysitter for a caretaker, and that no one was actually doing much in the way of housekeeping or household maintenance around that mansion, and probably Roxy being 'encouraged' to hire a couple housekeepers and maintenance people so that she's not doing all this on her own. And that Jake has so thoroughly vanished on his kids, and left Roxy as caretaker, is begging a really big question: what the hell happened to Joey and Jude between 'now' and the start of SBURB? It seems like Dad Egbert and Nanna definitely don't know Jake had kids, though I suspect Roxy wouldn't be having to handle this on her own, if they did. How Joey and Jude are related, though, seems to be in the same way that Dad Egbert and Dad Crocker are: they're technically half-siblings to the rest of the Crocker/Harley/Egbert/English family group. But nothing says Roxy couldn't have moved at some point.) (On the other hand: this doesn't seem to be where Rose entered from.
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And it'd explain why Roxy's so stressed as to be drinking heavily, because she's having to juggle two mostly-abandoned kids and a brand-new toddler, and probably can't just bring the toddler over because Jake has made the place a goddamn deathtrap as far as small children go. Which would mean that it's entirely possible that Jade has already landed and that's why Jake has so thoroughly fucked off - Joey says that the last she knew of, he was somewhere in the Pacific, but her information is a few years old. I didn't get a good look at the calendar, since I was watching it from a friend's stream (I'm going to be playing it tomorrow or the next day, depending on how long it takes me to get things up and running), but the nostalgia bombing and the existence of pogs as a thing Jude is eager to have around and thinks is cool has the year nailed around '94 or '95 for me? So the canon troll kids are definitely not the only ones (besides their ancestors) to hold those symbols, with the possible exception of Karkat.)
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(I also was really excited to see that band poster on Dammek's wall, though - one person on it has a Libra symbol, and the other visible person has an Aries symbol. Is it just because he figures his psionics aren't good enough? Or are Helmsmen not nearly as common-use as we thought? It's also interesting that, despite his (weak) telekinesis, Xefros is expecting to be shunted into being a butler - he's not worried about being turned into a Helmsman at all. Which means that 1) Dammek is at least a few months older than Xefros, possibly more, and 2) there may be a wide ranges of ages in the kids on-planet! What I'm interested in is this "Rites of Maturation" thing Xefros made Dammek a cake to celebrate his wriggling day early, since it was going to fall after when Dammek would need to go do those - which implies that getting shipped off-planet is a staggered thing, instead of the "one whole generation in a fell swoop" kind of deal that I've generally seen pictured. She definitely doesn't have the Peixes symbol, though. This is supposed to be at least one Heiress before Feferi, possibly more.
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