Run the screw in, take it back out, fill the hole with wood glue (or sealer of your choice) and run the screw back in.
I sealed the underside of my floor with glue, scuffed it, and intend to paint it after canvas, before attaching to the trailer.
I don't see a problem attaching the sub-frame to the trailer first them the whole cabin to that, so long as the frame stays square and doesn't rack (check that the measurements across the diagonals are the same before pinning it down). You need to wrap the canvas over the cabin and around the underside of the floor; and IMO it is better if that wrap gets captured when the floor gets attached. I suppose you could wrap the canvas under the edge of the frame instead, but with your cantilevered floor that won't really trap the canvas between the floor and trailer frame.
The proven method is to build the cabin on the floor off of the trailer frame, and then attach the cabin. No chance of lifting a canvas edge or flapping in the breeze. On the other hand, I guess it shouldn't be a problem either way. There are plenty of seams at the roof to wall joint that haven't flapped, so take your choice.