I would replace it all with an 8" cedar clapboard and use a solid color stain for the entire house, ONE color.

Here’s some ideas of different colors to consider. The first pic shows the columns as they are and the others show if changed to cedar columns.

Insurance is covering a full replacement of our siding

What is it being replaced with?

Porch and trim will also be redone at some point

What is "redone"?

What color is the roof and when is it due for replacement?

For the columns, I'd increase the size -- but no cedar.

For the siding, consider a varied exposure. Real wood shingles with woven corners always look good.

I like a subtle difference in color for a Craftsman. These are examples, but I'd probably go with a different set of colors.

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First off, I like the house you posted, except I would bring down the darker color on the sides and just leave the porch white.

I do like this combo. Lighter and brighter than expected on a Craftsman. Exact colors are listed.

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