Ouch! I guess you have one of those HOA type oversight committee.
The dried tan sticks, assuming they are perennials and part of the landscaping, should be cut down to something like 4 inch stubble so they can come back at a later season when it's favorable for them to do so.
I don't know about pruning the roses after Cynthia's post about different cultural methods. Why don't you start by individually removing the dried up leaves? Anything looks better after the dead and dry stuff are removed. It could more easily be done, I'm sure, if you wear protective cowhide gloves and simply run your gloved hands down the stems (the gloves *should* protect you from the thorns). Alternstively, you could try super blasting them off with leaf blower or air compressor.
The tree.... I really don't know about the tree. It doesn't look right in that space to me. It's too big and the planter is too narrow. Do you have any idea what it is? If you can post close up of the tree, even dried up leaves for he leaf structure and another one of the trunk for the bark pattern, someone here may be able to ID it.
DON'T PEEL THE BARK. Some trees have perfectly normal dry, flaky looking bark. Cut or shave a tiny nick and see if you see layers of green.
2 feet is very narrow space for any kind of tree or shrub unless you are training/pruning it as an espalier.
Mine aren't very well done since it was my first try, but those espaliered fruit trees against the fence to the left are growing in a 2 feet deep fence row bed. I have two pears, two apples, and a persimmon growing in the narrow space:
Since it sounds like you have to do some serious work, you might as well take the opportunity to dig down in an unplanted area and see if the planters have bottoms. That is going to significantly determine what you can or can't grow in them, and how you will need to treat the existing plants.