Once you paint timber, it will need to be regularly painted, thus the maintenance increases. Why does it need paint? What's wrong with the natural timber colour? The screen plant looks like the purple foliaged Dodonaea. This can end up really tall and rangy with limited growth at the bottom. They can also be short-lived so this may not be a good choice. Mind you they will last for at least 7 years. But with the screen in front of the timber fence, isn't painting it superfluous? And the brick wall looks fine. I think that if you take care of your screening plants - fertiliser, water etc, you will have a screen that effectively hides the fence well. So why not just wait? I like the contrasts of colour already present and would think very carefully about any changes. Maybe a change in pot colour and shape. The black pot is dull. As a professional, my advice to clients is to keep colour limited. Work with greens and neutrals and have minimal tho high impact colour. This way the limited use of colour is classic and really effective. Alison

I know it's been a while, but I'm interested to see what the end result of this was.

Hmmm, I agree it is important to take into consideration what is on the other side of the brick. It looks as if there is no insulation in that wall, unless as was suggested, it was an entry door at some point. You may want to consult an expert to find out if the brick needs to be sealed, made waterproof, etc BEFORE you drywall over it, although it looks perfectly dry. I like your idea of dry walling it over and creating shelves/TV unit. BTW, I like your timber flooring. What kind is it?

What is behind the brick wall? Hopefully not a secret chamber with a hidden body?