When I first saw this post, I thought maybe you were referring to Marvin, but then I saw you were addressing Skyraider.
That sorta segues into a point I wanted to make. Certain things trolls have done kinda have been done in frustration. Here's what I mean:
BlueSpike: I've made this point before, but I'll reiterate it. The general feeling is "BlueSpike is/was a little sociopath" and that he's pure evil for the stuff he wanted Chris to do. I knew BlueSpike well - I haven't heard from him in a while, he's mostly focused on his studies as he should (remember - it's not like he's going to eternally be 13 years old). I've played games with him, I've been berated by him, I've been insulted by him, he is a little brat at times. However, you have to kinda consider the circumstances.
BlueSpike was a 13 year old with maybe a dozen other people, who were significantly older than him. He was 13, everyone else was about 19 or 20, some people a bit older, some people a bit younger but he was still the youngest. He was the first sweetheart who could be "controlled" - he was willing to listen to what we had to say, Panda sorta worked but she's still sitting on a pile of content we'll never see if it actually exists as she pretty much took her toys and went home. There was significant pressure on him to talk to Chris like, every day. Imagine having to talk to Chris, every day. You might think it's an awesome opportunity but remember, you don't get to have an actual conversation with him, you get to hear him talk about how he wants you to visit him and have sex with him so he can stop being a virgin with rage and how you have to bear his children and you have to eat at a shitty buffet place as a fancy date. Plus BlueSpike had to endure several of those cyber sex sessions where he more or less had to deal with Chris masturbating to his voice. It would take a toll on anyone.
So when that final audio came along, it's so long I forget the exact circumstances, I sincerely believed he kinda snapped. He was just so pissed off at Chris, he just demanded that Chris burn his house down or shove a medallion up his ass. Here's the thing though - there was no way to capture any video footage BlueSpike saw. Afterwards, some of us asked him "Why the hell did you ask him to do it if you couldn't record it?" and he's like "I dunno." I believe in the released audio you can hear at least two people say "BLUESPIKE, STOP" during the audio when he tells Chris to shove the medallion up his ass. If it's any consolation though, the likely opinion is Chris just shoved it between his buttcheeks as he really didn't understand the difference between like, your buttocks and your actual anus. Again, none of this really justifies what BlueSpike did, but when you deal with Chris for so long, you might have a tendency to snap.
I think Kacey is a similar case as well. I don't recall her being a pleasant person to begin with, but I try not to bad mouth other people personally just because of some of the things they've done in the past. Anyways, while I think that part of the motivation of the berating of Chris was that that would be the only way he would listen, but I think part of it might have been she took it personally when Chris would say something to her and not do it. She took it as a personal offense and I think that's part of the reason why she was so harsh on Chris. Also again, the nature of having a conversation with Chris - you're not an equal partner in a conversation, you're expected to listen to Chris ramble about some stupid shit he thinks should be included in LittleBigPlanet or how it's crucial he gets laid soon so all of his problems can be solved. I don't think I've ever heard a conversation with Chris where he asks something like "So how was your day?" or "How are you doing today?" (please prove me wrong if there was).
Personally, I set extremely low standards for Chris. Maybe it's wrong but at least I don't get upset over something Chris does. I used to, but then I started doing that so when Chris says something outlandish or does something stupid, I'll be like "That's our Chris!". Chris doing something stupid is like a 5 year old doing something stupid - you don't get genuinely angry over something a 5 year old does, you might scold them but you realize they're a 5 year old and the bar shouldn't be set so high.
EDIT:
One aspect of BlueSpike I forgot to mention, mostly why I brought up the fact he was the youngest. I think part of it too was he wanted to impress the rest of us who were older, to be one of the "cool kids." Not too many 13 year olds get to be treated (almost) as equals by people older than themselves. I think part of the medallion thing was an attempt to impress us, though I think that just stress from having to deal with Chris played in as well. Someone in chat was skeptical that it was the only factor, which I can agree, but I'd say it's probably a contributing factor. I am however bringing up this point as I think that also played into effect why BlueSpike decided to ask to shove a medallion up his ass. I don't think BlueSpike is suffering PTSD from hearing Chris jerk off but I think having to constantly interact with him and having to get stuff that was amusing from him wore down his patience and that kinda made him snap.