Matthew,
We would need to further investigate what your Portfolios look like (via ticket as we would need access) but if you are using Fixed Price within your work plan, this will overwrite and affect some of the roll up values you may be expecting. Here is a good article that talks about the different Financial fields.
https://success.clarizen.com/hc/communities/public/questions/203996298-Work-Item-Financial-Data?locale=en-us
https://success.clarizen.com/hc/en-us/articles/205712708-4-7-Projects#financial-fields