This is certainly not going to be as easy as season 1!. Its still not clear to me whether season 2 will need 1 or 2 films. It depends on whether event in The Marshall become significant or not. If not then I agree with Jake by starting with the Heiress and hopefully it can be done in 1 film.
I loved the Jedi episode so it would be hard for me to cut any of that out. I have done a rough edit where the opening scene is moved and combined with the finale. Works really well as it adds suspense to Din locating her whilst keeping the kick ass Lightsaber scene.