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I think I'd put stainless steel carriage bolts in the 1/2" holes. as for the large hole, perhap you could have a patch welded into the hole, then paint and undercoat beneith the bed, and paint in the box.
Depending on the future use of the pickup box, I have seen both plastic and metal plugs at my local hardware store. But I think the bolt idea is the best.
Your best bet if you want the contours to remain the same are to call around to several body shops in your area and ask if they have a smashed up bed.
Easiest thing to do is go to the metal shop in your area, and by a piece of sheet metal and fab your own. Rivet bolt or weld it in depending on how smooth you want it.
Sounds like you had a B&W Turn Over hitch in your truck. Try to call some RV places that sell/install B&W (not RBW) and see if you can get a piece that was removed from another third gen dodge and have it welded back in (I saved mine for just that reason)