Without having to redo the canvas it should be a pretty easy build.. I was able to get the floor pack done quick and I am a hack, so with your skills it should go quick.
I don't leave mine on much as I need the truck for work.. honestly, after doing it a few times, I can get that thing on and off really quick.. Even though there is only 1/2 inch clearance between the tailgate space, I usually get it lined up right the first time.
I have mine sitting on a camper dolly/trailer thing and the way it sits I only need to lift it about a foot to put on..