My expectation - and hope - is that some new content is announced on Dovetail Live in a month. It is still only one route, with relatively few trains, so you will expect gameplay to plateau after a while. The more the game is added to, the less that will happen, not just in adding new services, but in making previous ones more interesting. I think a release every 2-3 months would be good for the game, and would probably work commercially. Most Thomas merchandise works the same way, it's about building up collections.
It's possible. I figure they weren't going to commit unless the first one sold, and it takes time to create a second DLC. Guess we'll see.