Unless you are changing all the sides I would stick with the same color that is there now.

I'd replace the window over the door with something larger that has no arch. Increase the size of the coach lights.

https://vinylshake.com/foundry-7-inch-split-shake/

Find the product you want to use and then begin to look at colors. Some manufacturers have scores of colors, others just a few colors.

What an interesting bump out. Looks a bit too heavy. If this was my project I would turn the whole thing into a two story porch that had been closed in- engaged columns on the first floor- ‘handrail’ around the second floor with smooth panels above and below. Connect the pork chops into a pediment. Paint all the trim color.

Look to do a judges panel treatment instead. More elegant and fits the style of your home.

sounds like a great opportunity to do an overhaul of that portion.

shakes, if you like that look, for sure an architectual feature either with new doors, window, overhang, or all. If shakes, weave the corners instead of corner boards for a professioanl look.