Dave,
If you a going to repaint the boat, why not add a access port? Those screws shouldnt have pulled out, they should be through bolted with washers on the inside. Getting stuck in weeds shouldnt rip out your pintles/gudeons. Thats bad workmanship in my opinion.

Cut a hole in the transome and add a port hole, get some bolts (not screws with washers on the inside and use nylon insert SS nuts with backer plates in the hull.

Bill