You would need to know your zone specifically in order to pick plants that work. However, when you're planting in containers, it's different ball game. Many things that will survive winters in your zone may not survive if in a container. You might find a list of plants that work better in containers but it will not be all inclusive, or necessarily even accurate. It's a crap shoot. I think some of your containers are on the small side for growing shrubs long term. Per your fifty-dollar container, I would pass and pick one made for plants. If you plant in that, you'd never get the plant out without destroying the container, because of the straight sides. Too, because it is galv. metal, it will not last long if planted.

The plant you have by the kitchen corner seems too close for anything woody. That bed better for perennials or groundcover.

Thanks so much for your sound input. I really appreciate your insight as I clearly know so little about this.

When a plant's roots are in the ground, they are somewhat insulated from freezing. In a container, they are much more exposed and will die in the winter. Evergreens can also dry out. I am planting hosta in pots for the first time, and will probably take the pots into the garage to give them a better chance to overwinter. http://www.sheridannurseries.com/garden_tips/container_gardening/hardy_plants_in_year_round_containers 

https://www.midwestgardentips.com/best-evergreens-for-containers/

some ideas using Rose of Sharon, Mahonia beali, Rodgersia, Jack Frost Brnnera, Nandina, Poets Laurel & Lobelia: (I am from Philadelphia....these plants will do well in the climate & sun exposure)

Sounds like a metal pot isn't the way to go. Philadelphia sees a lot of fluctuations in humidity and does the limbo often between freeze and thaw in the winter: 30 - 45 degrees often from day to day. The expanding and contracting does a number on foundations. Would this happen to pots as well if they are ceramic or terra cotta?

Also, does this temp change lend itself to one kind of shrub more so than another? Again, I'd love something that keeps its broad green leaves in the winter.

Save yourself money and grief, go to a local plant nursery and request an on-site review. Most will deduct the review fee from the cost of the installation. This is the busy time for plant nurseries, you will get a better deal if you wait until the Fall. Do it once, with a plan that has a good chance of succeeding.

Chiflipper - I'd love to do it once and have it work and am willing to pay for it. But as with most things in Philadelphia, I'm at a loss for finding a pro.

I live in the city. Nurseries I have gone to in the city have limited shrubs since there are no real yards here. Most nurseries in the suburbs don't come into the city - not even to deliver items you've purchased from them. I have had two different gardener / landscapers come here and they were just guessing as much as I was. Both installed gardens that failed in our dirt garden area - one transplanted into a container a dying shrub they placed in our garden. It didn't succeed in the container either. Our next door neighbors paid a hefty sum to a woman who specializes in city container planting. She built for them nice planters, for a pretty price, in which all of the shrubs died. I'm at a loss!

Gardening isn't like interior decorating. The owner has a responsibility to care for the plants long after the designer has finished work and gone home. Gardening is a continuous process, not a 'do it once and have it work out' job. I am wondering whether your neighbours did much to make sure their shrubs survived? I don't mean to sound critical but in your photo with the dog I see what looks like a very sad evergreen (rhododendron?) in a too small container. If the container was larger and the shrub had been regularly fed and watered there is no reason why it should not have thrived in that position for years.

Your space is so small that I am sure you could tackle it without a professional. Millions of householders in the UK have these tiny gardens and make them attractive without paying for help. Have you looked at any gardening books aimed at small town gardens? Anything by John Brooks? In a confined space fewer, larger containers look better than a hotchpotch of many smaller ones.

Floraluk - You are not being overly critical at all. The dead plant in the dog pic is of a skip laurel (I think aka cherry laurel) that one of the gardeners planted. I have been spying what neighbors have potted on their sidewalks and do see a number of rhododendron. I was thinking of trying to replant one in this pot black pot and am glad to know that it looks too small. I was reading online about container gardening rhododendrons and I thought they liked shallower containers.

I agree that I should be able to do this on my own and concur that just a few pots in a small space is better than a hodgepodge. I might also be trying to make happen something that cannot: getting a broad leaf evergreen to grow in no light over the winter in a cold climate. Perhaps the answer is it just can't be done in these conditions? Few things made me happier though in the winter than looking out the kitchen winter at this skip laurel the last two years it was thriving.

What about Bloom-a-thon azaleas? I am north of you and ours are doing well in a shady area, but they are in the ground. We started with 2qt size.

Isn't there a way to mediate the winter temps, without cooking the roots? Solar blanket? insulation?

https://www.monrovia.com/plant-catalog/plants/3463/bloom-a-thon-red-reblooming-azalea/

Dalton, does your azalea stay green year round? I need to learn more about solar blankets and insulation. Are those things that get added in winter and taken out or off in summer or are they down inside the pot?

Mountain laurel and some azaleas and rhodos stay green year-round. Most do well in part-shade. The plant next to the broom in the pic with the dog looks like a rhodo that's outgrown its pot. If you do potted plants, you need BIG planters. If the place is yours, I'd dig up some of the hardscape and put in a bed by the fence. If it's not, you might be better off with climbers and using art for winter interest.

https://www.houzz.com/magazine/how-to-choose-the-right-plant-container-stsetivw-vs~104807414

The Bloom-a-thons are evergreen and have pretty foliage. Last year Lowe's carried Monrovia plants, and they could be shipped directly to your home or the nearest Lowe's. Rhododendrons Direct allows you to sort by sun vs shade OR by zone, I haven't purchased from them yet.

I never used insulation for plants as all mine are in the ground. I was hoping one of the experts would speak to that.

April. Dalton is my cat. Disregard the weeds. lol