New answers tagged wood
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Use No More Nails mounting adhesive, and regular nails in combination (the nails clamp the parts while the glue is drying).
Apply No More Nails to both surfaces, and then pin the caster in place using regular nails. Between them they should provide sufficient bonding to survive anything that you could reasonably throw at them. No More Nails has a very thick ...
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Using a washer behind the nut on the inside would have been stronger, but it sounds like the castor plate is still secure, just the wheel broke off. Chris H's solution of adding more wood and using wood screws is a good mechanical solution, but the added thickness may ruin the illusion of the legs if they're supposed to look like they touch the ground.
If ...
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If you have good access to the outer surface of the wood itself (i.e. if it's not covered in fabric), I'd glue another 1/4" or better 1/2" layer of ply to the outside, and use woodscrews that go through both layers to attach a caster that has 4 screw holes. Use the fattest woodscrews that will fit through the caster plates, with a slightly tight ...
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