Owned a PUP for 17 years before upgrading to a TT.
Make sure everything is clear for the bunk ends to slide in.
Undo all outside fastners.
Undo all elastic banding holding the bunk end fabric in place.
Drop the roof support bars to pop out ends.
Push both bunk ends in.
What I would do is lower the roof (at a pretty good pace, but I had 17 years of practice) I would get to the point where the roof is about 12" from the main body and walk around tucking in all the fabric.
Continue to lower roof until I got slack in the steel cable. That tells me that its not going down any more.
Walk around the trailer and give any exposed fabric a final tuck and simply lean on the roof while you latch each corner.
Should only take about 10 minutes.
Also with the awning, I would unzip the bag prior to raising the roof. (i had a velcro strap in the center of the awning, inside the bag to hold it in place.)
And at tear down. right before I was ready to lower the roof, i would fold up the awning legs. (it was a nice awning, no strings or poles. it was a carefree of colorado. very similar to what on most TT's) I would let the awning hang and lower the roof to a height that was reachable for me to roll the awning up and tuck it inside the bag and zip it up. I then would continue with the tear down process above.