Jay has a great sense of humor. Comedy is best when punching "up" (in this case, to the dominant secular ideologies--not so much at other "heretical" Christians). Some weaknesses: Gamma-ish ("lol" at everything); tendency to get into internet cat fights; can come across as legalistic (Pharisee-like); avoidant of the J-Question; and his connection to Intelligence asset (and tranny-loving) Alex Jones.
I see his true calling would be having a production company focused on sketch comedy, memes and comics. He has a deep grasp of philosophy and theology and the ability to explain difficult concepts in a simple and often funny manner. Academia is a sewer, so he will never be recognized in that arena (and should pay them no fealty).
A good secondary business for him would be as a publisher. For example: writing/compiling a series of religious commentaries would be welcome. On at least one his casts he was using a book that was out of print for several years (he should license and compile such work into his own volumes). He could also make great textbooks for home schooling, such as on metaphysics.
He's married, so perhaps his priorities will change after he has a little Jay/Jane. As I get older/wiser I find it best to never put others on pedestals. We're all flawed humans. It's always easier to tear things down than build things up. A better Christian attitude is to focus on helping others in their journey towards theosis.
Regarding the highlighted in bold, I agree.
I read your post with great interest. I'm someone that's been involved with and interested in, both God and comedy/humour - especially sketch/improv - ever since I was young, and this is probably what interested in me Jay's channel initially.
It would be my dream job to write sketch, or to be paid in comedy (lol)..... I think Babylon Bee do it well, and of course others, in terms of satire.
For some reason, comedy entails vulnerability to really relate, or provide truth. The audience knows in a second if you are being sincere or not. This can of course be dangerous ground, which is why I think it can take less "courage" to share "correct" biblical arguments. You have something to fall back on. Let's say Jay, in this example, can stand on the shoulders of a great church history, theological and philosophical arguments. This might be a reason Jay moves towards less comedy, or maybe not, only he can answer.
You can only do that - build on others foundations - so much with comedy, because it's always new, evolving and much more grey. It is however massively important, and something i'm deeply interested in, especially when it comes to proclaiming and revealing Truth.
My two cents.