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My green b pillar had some pretty bad rust issues on the skin. I swapped it with the one from the tan pinz and painted it fir the new owner, but now im left with a "wholey" pillar. It's way too much to bondo and quite a bit of patching and drilling, so I was thinking of totally reskinning it.

Has anyone ever attempted such a thing?

I've just "de-skinned" a couple of bars so I can use the extruded "door shut" section for a K body......I drilled out all the spot welds.
Re-skinning it shouldn't be a major dilema, as if you haven't got (or can't get) access to a spot welder you could plug-weld the sheet to the bars.