I am going to say your issues were with how you set it up. They work perfectly together and you don't need gulp since it's just a task management tool.
Yep, there was mostly a problem with setting up product pages through gh-pages. The relative and base URLs would break and so I had trouble with Jekyll. There was probably a relatively easy fix except Middleman just sounded like a better choice for me.
I am going to say your issues were with how you set it up. They work perfectly together and you don't need gulp since it's just a task management tool.