John you are fortunate to have such a yard, although the tennis court does aspect as a divider breaking up the space, I think this creates an opportunity to create garden zones or rooms. Intimate garden spaces can be individual enough and still be integrated into a larger footprint. Your garden perhaps may be viewed from different windows, and have different aspects, therefore will have different requiremnts of sun, shelter etc. As the second picture appears to have a shed or structure, and looks more of a utility space, I would obstruct the view from the court, by planting a Boston ivy to cover the fencing, providing a delicate hanging foliage wi ever changing colours of reds and greens. I would do the same on the opposite fencing that overlooks the main lawn area, although I would create a large window effect by clipping or restraining the creeper from a large square in the centre fencing section. Tis will create a room with a view in the foreground, and with effective and clever planting, lighting and design elements, you will create an interesting viewpoint that will direct interest into the yard beyond the court. In the background, the timber fence I would plant your murray a hedge, so the small blooms will soften the look of the fence, paint it a dark colour, like domino by dulux so the foliage stands out against it, and gives an illusion of a deeper boundary. In front of that, centre to your created window in your fencing, place either a sculptural element, in the form of an urn, a formal topiary or statue, perhaps a small water feature with lighting, so it extends the perspective yet again. With the green hedges now creating the walls of your garden room, plant your chosen iceberg roses in front of that, and some informal plantings below. I suggest a bench to watch a match or two, and utilize the other garden Rea to house things such as your patio furniture. Garden rooms don't necessarily make a space smaller, rather they may invite you to meander through garden rooms with beautiful elements and relaxing places to sit. I would also like the look of manchurian pear trees along the fencing if you don't like the idea of a creeper.

All climbers/vines will take over in time (particularly in favourable conditions) so they need to trained, plus keep an eye and secateurs handy. Angus' website mentioned earlier gives some pointers on selecting potential plants, including Pandorea. Also search up stephanotis (AKA Madagascar Jasmine, Hawaiian wedding flower, Bridal Wreath, Waxflower) - a beautifully scented and attractive vine.

first things first - 100% agree with Retro - don't focus so much on the nitty gritty on the cosmetics for now, rather focus on an overall masterplan for the property as you said the residence requires renovation. How you manage the stone walls to the pool is honestly the lesser of your issues here (you can deal with that one way or another depending upon certain preferences and budget............but clearly the bigger issues is the obvious awkwardness of the pool location and access in relation to the home - most likely an afterthought dropped/squeezed in the back...... what you have here though is great opportunity to improve the relationship of the interior and external spaces - this is way more important as a priority as it will make the most difference in terms of your overall living experience/enjoyment/functionality (and property value one way or the other) than the cosmetics. So if you can't see how you're are going to achieve that yourself, I'd be suggesting you best seek some Pro design consultation that deals with the renovation scope & covers consideration of landscaping /external elements/spaces that properly negotiate the site levels and better link/integrate everything in together....of course budget is always a critical factor/controller.... Hope this helps steer your focus in the right direction.... Best of luck PD :)

Absolutely agree about hedge... Leave it but have it trimmed and add trees to courtyard. I would decide on colour scheme first by painting large pieces of cardboard in a colour suite to complement the brick. Draw out lighter colours in brick & tone down with white to match look.... I would not personally use white paint as your brick is so dark.... Think cohesion not contrast... Ideas above re gate, letterbox, etc are excellent and another way to add interest... Also think about changing driveway colour to match house/garden as it is a big slab of grey... Your roof is dominant too...... Maybe get that done rather than rendering house walls.... I would look on houzz for ideas.... Look up Prairie style or Frank Lloyd Wright or Fallingwater his most famous house for colour/style ideas.... Or Taliesin West for anchoring house into land innovatively. Paint that chimney flue to hide it!!!!!!