I have made this point in chat a few times and I will make it on this tread too.
One of my biggest problems with "Chris Trolls" is that too many of them wind up getting careless. I have seen and even heard of recent instances of "Chris Trolls" doxing themselves and making themselves extremely vulnerable. Chris is a high-risk/low-probability of reward proposition. He is high risk, because he is still highly observed thanks to the nostalgia factor and Chris's level of paranoia towards now nearly everyone. If you try to troll him - you can expect your actions to be observed and scrutinized by a myriad of other people who are used to gathering information. Many "Chris Trolls" want to earn a name for themselves and often the only way to approach Chris and earn trust is to expose part of yourself in the process. This is very very risky. Simply because with the large number of people watching, you will get doxed either by Chris(+ white knights) for exposing too much of yourself or by all the other people watching him who are jealous of your access. Think of Chris as an object of a cult brand of fandom. This fandom is very determined and will jump on you for getting too close to their "Pet".
The low probability of reward comes from Chris's lack of access, paranoia, and the large amounts of info/content that have been extracted already. Even if you gain access to him, there is not much you can get that has not already been plundered or that is even remotely satisfying.
Chris has improved as a person to a degree(I will admit how much is up to debate). I would argue that Chris has had a baptism by internet fire and life events. The Chris of today is not the same guy as he was in 2008. 7 long and punishing years have passed. Chris has lost his/her father, gender identity(I have to use his/her on everything talking about CWC), desire to make Sonichu comics, faith in humanity, desire to complete school, a lot of health/lifespan, hair/youth, desire to make youtube videos, house, pets, belongings, and a number of other things. Chris retains the desire for a mate and faith that she will come, but a lot more has been lost from Chris's life.
What more can you take from a person who has lost so much?
What more can Chris create for you?
There is an extremely low probability of any reward for trolling him/her at this point.
Even if you wanted to just become a friend and not troll him that is very very hard. There is no access there and really nothing Chris can ever give you.