How about going a few notches up on the chip from the cream white trim to a light tan/brown. It would match well with the siding and the door IMHO. Its hard without seeing pictures of the house.

I would do the ceiling and the columns white. I would do the ledger board and the deck a taupe/brown gray like Sherwin Williams Manor House.

One way to make window boxes low maintenance is not to fill the box with dirt but to put dirt into small pots and planters, root the plants in those and then put those inside the window box. With any window box or planter, frequent water and good drainage is most important. If i had just bought that house i would simply lighten up the porch woodwork, probably with a light green sage, but maybe some type of white. Then i woud live through at least the entire summer before making landscape and facade changes. The house is perfectly respectable as is, so no need to rush. You’ll know a lot more about how light affects the house and flower beds other things if you watch for awhile and you’ll end up with a better design-if you wait for more info.

Interesting idea, covering the steps with pavers. That would bring the height of each step up if you put the pavers on the step surface. You could get one and measure the new surface height. 7 inches is standard. YouTube videos you can watch. Here's one.- Look for the part that might apply to your steps. Not rocket surgery.