Additional photos

I agree with the trees being removed. I really do like the window box planters. I think when I can get over to the house and can plants in them I think they will add a lot.
Thank you for your response.

I think the window boxes will look great once you paint the legs and I might also use some "spill" (trailing) greenery to make the painted legs even less noticeable.

Go to your local garden center and pay them a few hundred $$ to design a landscape plan for you.

The window boxes look very shallow, more like trays than boxes. How deep are they? The left one appears to have no back meaning the wall will get dirty and possibly damp. What are you hoping to plant in them? They only look suitable for shallow rooting subjects like succulents. Do they have drainage holes?

Personally I dislike them but since you want to keep them you'll need to address these practical issues.

The planter boxes aren’t finished yet. I plan on using succulents since they grow so well on the central coast. These are some of the ones I want to use.

The window boxes do look shallow, but I agree painting the legs should help, along with plantings in front of them. We’re inland in Southern CA. If you’d like some color, I’ve had great success with ivy geraniums in window boxes (not the zonal variety). They grow up, out and over with year round blooms...very pretty. However, our boxes were fairly deep, and I’m not that familiar with succulents.

A path from your porch to the sidewalk with succulents and other drought tolerant plants like CA sages on both sides would look great!

I love the simplicity of this one too. So many options!

Here’s an updated picture from last week. We took out the two trees.