"Before I went to all that effort, I'd just paddle it backward from the front seat"

don't think that would work very well at all, with the differential rocker - would probably work better paddling from the stern seat with most all the gear far towards the bow for trim

my thoughts are you should just rent or buy a dedicated solo boat

and at the least, take that boat out on the lakes and see what heppens when you paddle it solo in the wind - I'd think it would be hard to control and hold a course in the wind