Best Practice: Lofting/Boundary Solid/Surface?

I am looking for the best way to complete this solid model. I am not having luck using the loft/boundary solid or surface techniques. The geometry i am trying to accomplish seems simple to me but i am struggling to get there. I have a skeleton of sketches outlining how I want the body to be filled in.. The Images attached and the solidworks file will hopefully help describe what I am trying to do.

I couldn't attach it because the file size was too big but here is a google drive link to the file: Eearbud A.SLDPRT - Google Drive

Thanks,

Nathan

SolidworksParts And Features