I have a working theory on why he decided to put on the voice, and in general about Jason. Long sperging ahead so forgive my niggertude.
So we have lil' Maldy beginning to work for blizzard right? He's a nepohire, but he probably has some big dreams. He's an ass, but nobody can tell that to him because nepotism. He's young and has his whole life ahead of himself.
After years of just QA, the best he can advance is career is in cyber security, and not as a l337 h4xx0r but as the guy who sends you an email saying you won a new car and you're not supposed to click it. He realises this is not what he wanted, even though it was on him to improve in game development and not be a lazy nepofuck.
He does manage to make Champions of Breakfast however, proving to himself that he can actually make something. This is a big ego boost.
Ok, now what? "Should I finally start putting some effort and work towards becoming a better dev? No! I'm a programming God! One project is enough to prove to myself I can finally make Undertale 2 and live off my magnus opus just like Toby Fox!"
He begins working on Heartbound and releases it on early access on 2017 to positive reviews. But uh-oh! Turns out Toby Fox WAS working on Undertale 2 in the form of Deltarune, and releases chapter 1 later that year.
The difference between Deltarune ch1 and Heartbound is night and day. Ego down! Mald reverts to an insecure college dropout that finished highschool just 2 years ago. Except he's over 30 and that's pathetic.
Maldy feels that way because he did not, in fact, do much with his life. He's past 30 and has done fuckall, and accumulated little experience in what he wanted to do. Even after leaving Blizzard and padding the fuck out of his resume, he feels insecure and small, especially after seeing the difference between DR and HB.
He needs to prove he grew up and get back out there, so he starts working on himself and getting better at game dev and programming.
Just kidding! He starts voice training/bass boosting his mic or whatever to feel older and accomplished.
His wimpy twink voice become what it is now and he feels like a grown up. Now THIS is how it feels to be a grown up!
It's a huge ego boost. As he begins streaming, his ego grows and grows as he listens to his new voice becoming deeper and deeper, and as he talks about his past he begins rewriting it. Every little thing he did as a nepohire? Actually a huge personal achievements (social engoneering emails at Blizzard -> l337 h4xx0ring powerplants n shieet) and proof that he has come a long way since highschool. Lie lie lie, ego boost ego boost ego boost.
Then he manages to exploit the YT short system (imo with the help of a talent agency) and the rest is history.
Into this timeline (I might have jumbled up some events) you can fit anything that has happened to him: working for the government "hacking powerplants" (in reality as a contractor probably doing something completely different), his Second Life business history, his EVE "career" etc. And most follow the same pattern: Maldy begins "working" with something, his ego grows, he encounters social pushback because he's a complete asshat or something happens that blows his efforts into shit (his EVE clan getting BTFO, Deltarune's release etc), he shuts down then leaves the premises of the situation, leaving a horrible impression of his character to anyone involved in that situation.
In conclusion, Jason is immature and thinks his voice and Mr Rogers character are proof that he grew up, that he has accomplished something in life.
It's also why I doubt he will ever troon out, because it would mean to go back to his wimpy, post-highschool self. He had a privileged start in life and squandered it because he's fucking lazy and full of himself. All he had to do was to be more humble and have more drive to do things such as improving himself.
I don't remember in what general thread it was written but iirc one characteristic of lolcows is that they have something you can recognize yourself into. I won't go into details to avoid TMI but his laziness and inability to grow his skills (coding, writing, anything really) somewhat speaks to me. Maybe there's something I'm doing wrong with my life and I need to wake the fuck up.
BUT HEY, THAT'S JUST A THEORY
A GAY THEORY
THANKS FOR MALDING
TLDR: Maldy 100% rapes ferrets with the bathroom gnome.