I absolutely believe in our writer/director/star's talent to make another Waitress. As an indie filmmaker, I am a realist and I never like to get too excited too soon. But there is a wonderful excitement brewing all around this project.
With the casting, I am negotiating with each cast member through our casting directors and the actors' reps and it can get complicated very quickly. I have done enough deals to know most of the deal points and what is feasible for a film this size. It can get overwhelming pretty fast so you need to figure out a way to keep things consistent. I do recommend that filmmaking deals be vetted by an entertainment lawyer.
A lot comes down to using Favored Nations language as much as possible or carving out certain roles that may have a slightly more advantageous position. On Take Me Home, our writer/director/star is being carved out from Favored Nations as he deserves a stronger deal due to the many roles he has on the project.
Often, casting negotiations can occur all the way up to the cast member arriving on set and many times, after. Of course, you don't want to be negotiating after a cast member wraps but sometimes it happens. I try very hard to negotiate prior to arrival on set or at the very least have something writing before wrapping the actor.
At a bare minimum, you need to get some sort of appearance release for the actor's image. You need to know that you have the rights to their image so you can sell your film. From there, let the complicated negotiations begin!