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How would you fill this hole?

How about just replace the column. There is a ton of work to make that old thing look good, it is not just the hole. You will use a ton of bondo and primer.
 
I’d cram it full of hardware cloth or something similar for a backer, then bondo, the stuff without the fiberglass hairs. Sand and paint. That’s how I repair things like that at work.


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First things first...kill the rot with boric acid. Filling it with body filler may be a good idea except that wood moves so much with the weather compared to the filler that you may have to make repairs prior to sale. Just my $.02
 
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