It could also be because he is now just one person. Himself.
So, in episode 1, Tom was trying to depict "Show Within a Show". It didn't really work. However, in episode 10, there's a scene near the end in which he is watching episode 1 on his laptop. He's watching a show while he's in a show. It took ten episodes, but they finally managed to depict "Show Within a Show"!
Made better in that episode ten is when he finally gets how to make the show we're seeing.
There's also how the trope gets protrayed. The entire show is nothing but Show Within a Show, so of course Tom and the others start coming up with blanks.
In regards to The Reveal of Zack's dad, Mark being the Other Wiki's Director of Transmedia. The reason why Tom and Dana haven't found out is simple. Tom only knows Mark as Zack's dad and has paused each  episode he's watched before the credits. Dana only knows him as the The Other Wiki's Director of Transmedia and almost met him as Zack's dad from behind in The Ace. Zack in this case fails to realise how important this detail is.