I always push it into position by my self, I guess the only suggestions i can make is to ensure you don't have bedding pushing against the canvas, after you remove the pole try & fold /pull the corners of the canvas over as far as you can, then don't be too concerned about tucking the canvas in until it's nearly all the way up as for me at least it seems to tuck it self in especially on the right hand side I never have to tuck it in.
I push mine up far enough that I can step over the drawbar & just have one hand on or near the bed base as I'm crossing over to check the canvas