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Sounds good.
I noticed the round dabs of adhesive, but thought it was worth flagging.
Sometimes the original designs weren't all that.
I cba to explain each thing, but my folks place is Georgian, with their place started in a recession and the rest of the terrace finished a decade or so later. There are loads of original bits that unfortunately require regular maintenance regardless of how well they're repaired.
I'm going with the removing loose wood, treating with hardener then two part filler. While I like the idea of the brace, I reckon the weight of the whole thing and the inclined plane of the curved section would mean it would have to be either really well constructed or massively over engineered. The cost of getting either thing wrong is just too much to think about.
@hugo7 there was definitely zero consideration given for any protection when adding the skirting pieces. They've just been dabbed on with a bit of adhesive. If I get the filler right and shape it properly, it should be better at convincing water to fuck off away from the base of the post. I'm thinking four plain sides, slightly angled in at the top with a smooth/slightly rounded transition at the concrete.