I would try to make a gradual stair type planting area. on each level place pots to grow plants in. In a small space I have made gradual plant steps. This allows for more space vertically.Putting tall plants on top then gradually putting smaller ones on bottom levels.

For $100? Maybe swap out the chairs with some that are more modern but a real bargain on craigslist? The existing chairs are cool, but they tip the eating area in a distinctly un-modern direction. The table is simple enough that, if you paired it with modern chairs, that whole area would look modern. Sophie's advice is good too. Make sure you have extra flooring so your future remodel is easier.

Just don't crowd too much into the wall space. I would measure and plan to leave 25% of the wall area on each end empty as a "frame" for the grouping. You can go with a loose,mixed arrangement too if you don't have a set of identically framed pieces.

Have you considered a galvanized metal standing seam metal roof (if in your budget)? That would be more energy efficient (and maybe qualify for a tax credit or rebate--mine did about 10 years ago). The lighter color roof would contrast nicely with a dark charcoal paint. And definitely consider a new door--maybe a three or four-light modern door--with a nice pop or color--red is an obvious choice with the red brick. If you decide to stucco over the brick, any vibrant color would look good against the dark paint. I like the idea of using horizontal wood too, as another poster mentioned. Also, consider using house numbers with a modern font placed either above the garage, horizontally or maybe next to the the garage, vertically. For the house numbers, choose a metal finish which contrasts the color of the paint (eg. dark paint, brushed nickel numbers or light paint, black or bronze numbers. Also consider a downlight, like a modern sconce to light the house numbers.