I think after the big overarching plot that happened over MI2+Curse+Escape+ToMI, it's time to have a breather and go for stories that can stand by themselves. That is, release episodes that aren't connected to a longer season.
- It allows Telltale to give us more Monkey Island. Just sprinkle an episode here and there between and during bigger projects, but such an approach could add up to more content than we would get otherwise.
- We could get to see more interesting locales that could be fleshed out better than they would be in a feature-length story.
- More in-jokes for Guybrush. Better opportunities for smaller advances in character development.
- More standalone episodes means more opportunities for the writers to take risks and go somewhere interesting. After five games, the Guybrush+Elaine+LeChuck triad that pushes the plot is starting to look too much like Nintendo's triangle of Link+Zelda+Ganondorf. One could even experiment with different protagonists in the odd episode or two. It can also get writers out of the trap that plagued the Pirates feature films: the need for a longer plot that can make no sense.