a clarification, please.

What are you planning to paint? is it wood & brick front , side and garage?

where is the vinyl siding?

What direction is the brick planter (current gravel box)?

I would paint the verticle wood siding SW Urbane Bronze or SW Polished Mahogany

and plant Azaleas in the raised Brick Bed.

I like your landscaping. It's not too overgrown...yet! :) Works well with your house design/topography and you don't have an easy one to landscape.

Does the planter get any light? Does it have irrigation? Are you sure your kids are done with it?

If stuff won't grow in it and you don't want to turn it into a full time sand box, maybe cap it and turn it into a long long bench/potted plant shelf?

Thr brick planter doesn't have irrigation and it is under the overhang. No lighting in it either. Overall laughter exposure is low as it faces North. My husband had just proposed the cap idea too. I just worry it will look more like a loading dock for packages. 

An the vinyl siding is along the garage side wall, the back of the house and the far side. I'd love to paint all the wood, and possibly even the brick.

IMO the brick is the best thing on the front of the house . I never like beige with brick , have you looked into apinting the vinylthere are good paints to do that. I love hostas in shady spots so I would try those there in thta planter . I think a bench type seating will look odd,Judy for reference this is one of my fave colors with brick .

I would pull everything off the short (window) side of the house and replace with siding laid horizontally. There are three materials with three different patterns plus the two windows and it’s just too busy. I love the brick planters, how much time do you want to spend “gardening?” Will the kids play in it?