I'm all for Miss Jessay fucking up the only thing that has ANY long term impact on Chris's life: Sonichu continuity.
That's a really good point. There's very little that you can do to Chris through trolling that will stick with him.
Off the top of my head, there's only been a handful of trolling events that Chris still bitches about by name today. I mean, if you ask him, he can probably dredge up the more obscure ones, but it's rare that he'll bitch of them of his own accord. (Heh, one of the things Chris does bitch about without prompting is how trolls made him do the cakefarts video. He whines about how he spent a whole $9 on that cake, and he only got to eat one slice before he planted his pasty ass into it.)
And one of those things is how trolls fucked up the Sonichu canon. You can mess with Chris by just pointing out how he still has troll written characters in Sonichu. Or how there's a giant wart on the continuity of Sonichu from when Chris was forced to kill Simonla. That one still haunts Chris to this day.
Here's an idea: in the future, just translate curse words from other languages and use them as names for fan characters. Like, I don't know, translate "dick sucker" into chinese and try that. Send the characters to Chris, and if they're cool enough (from the perspective of an autistic manchild, anyway), Chris will naturally steal them and put them in Sonichu.
Voila. Now people can mess with Chris forever about the legacy of the Sonichu known as Dick Sucker. Chris would get madder and madder about having being tricked that he'd eventually write them out of the story or do something to deal with the canon issues. And even when they're gone, he'd still have another wart on the story.