Thanks Dave and Peter - your responses are helpful.
You are correct, my goal was to do a server side 301 redirect from the old domain to the new domain with the hopes of passing on SEO benefit since the website theme is similar (but targeting different audience consumer vs retailer). I understand that the poor user experience of this is now likely hurting us since the same relative path does not exist.
I'm going to remove the 301 all together since it is not helping us, and very possibly is hurting us.