What a fantastic architecture. When you do the brick, if you stain it with masonry /concrete stain you won't have the same issues of maintenance as with paint. They will spray it evenly - through you will have to select a deeper color - either taupe (brown-gray) or a straight charcoal. Love your windows and the classic angled railing. I think a dark gray on the siding will make the orange brick jump even more. What bothers me is the white (railing, fascia, eaves) juxtaposed with the earth toned stuff. So I would recommend camel tones - for the siding - something like http://www.sherwin-williams.com/homeowners/color/find-and-explore-colors/paint-colors-by-family/SW6108-latte/ and the hopsack next darker tone for the garage door. Use the lighter tan for trim that is now white - http://www.sherwin-williams.com/homeowners/color/find-and-explore-colors/paint-colors-by-family/SW6107-nomadic-desert/ Use the darkest tone if you are painting concrete steps. If you think you will stain your brick charcoal, then the white eaves and trim are probably right, and you may not want to paint it tan now and then go back. If your brick were charcoal, then I would block out the rest in grays and blue grays - leave the white eaves, but take the railing and posts charcoal too. A blue gray door - like sw smoky blue.

We had a landscaper come in and draw a plan. Re-used the whole bricks into a grid pattern, and filled the squares with concrete. This summer's job is to build the bench seats around the outside for a seating area. The flat surface has been great for our children - they learned to ride their bikes out here, and love decorating it :-)

I would clean up first. Especially the stuff growing in the paving. Then get gardening with pot plants and start experimenting with different plants and the positions. See what you like and if you can keep it alive! Our house has the sun setting over the back fence and we've done a few inexpensive things to reduce that issue (most expensive were outdoor blinds around the verandah) but for most of the year we just don't want to be out there. It is hard work to keep the plants going in summer, there is a lot of sand due to the difficulty in keeping lawn alive and it is just bloody hot. So, that's why I'm saying clean up, start gardening small and see how you go before committing to structures that might not address the real issues you have with the yard. Just my 2 cents! :)

It is a pretty 'basic' look , but unless you spend big dollars , that is going to be the base you are working from . the first 2 things I'd do , is buy a waterblaster , blast everything especially bare timber ; and secondly , do every fence in a charcoal stain . Personally , I wouldn't paint the bricks , and I'd even hold off painting the block too . That brown peak has to change , I suspect I'd go a mid-Orange , to be reasonably 'sunny' . Red or yellow too bright for the cream and the style ; blue or green too old and too cold ; grey too boring ; black or brown too dark . I the short term , I'd leave the terrace panels , but do the top rail in a bright Orange , and the base timber that can be seen , in a charcoal . The stair railings I'd do in white with the same bright Orange top rail , the actual stairs in charcoal ( you may have to add a white bit at the front of each to meet Health and Safety regulations ) . Windows etc are okay IMO , but add a detail or 2 -- 2 matching $100 letterboxes ; your street number in a nice style , painted bright orange or even apricot , made from ply , and screwed or glued so it is 30mm 'out' ( protruding ) from the downstairs wall between the 2 windows ( maybe off-centre by 30cm for impact and interest ? ) OR maybe on the front fence . Then your idea of plants in big bright pots will really add too . There you go -- $2500 and some labour and some fun and it will look quite a bit better .