Where are you located? In my zone 4 it is difficult to find things that survive year round in any type of pot or raised bed because the roots are exposed to colder temperatures and more temperature fluctuations than they would be if surrounded by soil.

if you are in an area where it is possible to have shrubs in a pot of some kind, you want the top of the pot level, parallel with the base of the window. So I would suggest either a base that will allow the planter to sit flat or a custom built container which will accommodate the tilt of the drive and allow the top to sit level or perhaps a set of smaller planters.

You may be able to keep the potted plants in the garage or in a protected space to avoid repurchasing every year.

I don't get why growing in containers, especially in a cold region, is perceived as being some kind of advantage. Seems to me it only makes things more difficult. Here, I was thinking coppiced red twig dogwood and some kind of groundcover.

Yardvaark - I have no choice really in the containers under the window near the entry. That area is cement and can’t be removed because of cost and drainage. But I LOVE the red twig dogwood idea!

OK. But that is one odd and mysterious arrangement.

How deep is the bed under the window? As in distance from paving to house?

The pavement goes right up to the foundation of the house under the office window (right of entry). The flower bed under the garage window is 30” or so.

So no dogwoods and ground cover in front of the office then. And as mentioned earlier sloping concrete = sloping planter, unless something is done to correct for this.

What is the material and shape of the darker area under the window? Is there some way to mount grow boxes under the window along that wall?

It’s all stucco. That may be an option, I’ll have to ask my husband about it.

Just one idea. I would ask someone who is handy, like a deck builder, to build a bench under that window to the right of the door. They can build the bench to have longer legs on the right than the left so the surface will be level. Then paint it to match the house or paint it black so it sort of disappears. Arrange pots on the bench.

My husband just had shoulder surgery or I’d be making him try his hand at some of these ideas! Thank you all for your insight.

Too much finger wagging?

Embothrium - too funny! Unfortunately, he destroyed his rotator cuff in a bad fall on the ice in February. Luckily, he got the surgery before the Covid shut down.

I did find this bench/planter box on Pinterest by chance today. I like it very much. With a little customizing - I think it could work!