ooh.... now this is a good theory! He does call Cheryl his "mentor", so maybe they came up with the idea together to help increase "interaction" in the comments. Shes a cast member... maybe she booked him the room with her discount, and was gonna stop by for a glass of wine like you said. and they decided "lets not show your face, it'll get more comments"
And to be honest, I actually had the same thought about the Hollywood studios video, that maybe they were just getting together for dinner, and just decided to not put her on camera.
On Twitter, hes "never been more content with life" so, theres that. I bet thats fun for Lora and Taylor to see, after all the work and time they've put into his channel for him over the years. All the sudden NOW hes content?? This guy...