Hey Claylyn,
I think there may be a trigger issue. Generally I would do an enrolled contact and an associated activity has the call outcome rather than using call ended as a trigger. That way you can do multiple branches based on outcomes and segment accordingly.
Regarding the line items being added, they way I have things set up is to attribute amounts as they are created through a rollup of certain fields that then populates the amount. Once the deal is closed my team add line items so we can report off line items for revenue info.
It would also be worth looking into enrollments and action logs and seeing what was enrolled and if it stopped at a certain step. Happy to jump on a call and help run through if you needed!