Thanks for the input everyone, maybe I should of added a little more info. The aircraft is privately owned and it is simply a case of fly it whenever you like as it hardly gets used, I'm such a lucky person!
We could even change the scenario slightly but the answer would almost definitely be the same.
Lets fly a short cross country, I, the insured pilot will fly there in the left seat (so far so good), on the return leg, the uninsured pilot will be the handling pilot in the left seat. I am not an Instructor nor is there any form of training/checking out on type taking place on the return leg.
I have actually had a right seat checkout so RHS checkout completed and I'm insured too but the handling pilot is sitting to my left. Any further input would be great.....I'm off to continue scratching my head