I have never eyeballed the bunk end handles on a Roo so I'm shooting from the hip, so to speak. Just looking at your pics suggests that the metal on the trailer is too thin to withstand the force generated when you open the bunk end. This is a possible fix, assuming you can get behind the "stripped" hole.
1)Remove the handle assembly from the trailer.
2)Install a backing plate behind where the screw has pulled out, large enough to amply cover all of the screw holes. Use an adhesive (maybe something like JBWeld) to secure the backing plate in place.
3) Fill the outside part of the hole with JBWeld and smooth.
4) Use holes in handle to mark locations of screws.
5) Drill new holes using appropriate size bit.
6) Apply an appropriate caulk to the new holes and reinstall the handle.
Hope this, or some variation, helps.
Happy Camping! ///// Richard D.
2006 4x4 Ford 250 SD / 2007 Flagstaff 827 FLS
One very patient wife and one furry child who travels with us. Forty-two years of trailering and camping, and I still have a blast.