Thanks for the comments, very helpful. I'll try to address each question to add more clarity.
Yes, the stepping stones area will be natural grass. I don't mind the little bit of extra work as I do not want to cover the entire yard with pavers.
Outdoor living space will not be covered. The table and chairs area will be. Was considering instead of a gazebo, purchasing a large patio umbrella that can pivot and swing to cover either area. Is this possible? I think I've seen them.
The lilacs are placed to provide a screen from my rear neighbors. The homes are literally 30' from that tree line. Ideally, the trees need to be 20-25'. The other areas aren't as neccessary because the dining area would be covered with either a perogola, or a large umbrella as mentioned.
The retaining wall is needed as I have a drainage swale. It's not very big. It will start at about 4-6 inches tall by the pool area and probably around 2' high by the cabana area. Will likely be a poured concrete wall with a stone veneer. Haven't decided.
Have checked for setbacks with city already. I'm OK. But will definitely double check again once I hire a contractor.
I currently have one child. 4 months old. Access via sliding door by the 'breakfast area'. Cabana door position likely on the north, or east side. Also haven't decided.
As for left side of pool. There isn't much I can do with pool placement. As per our by-laws The pool cant extend to the 'side' of the house. But you make a very good point. Will see if I can add another 2-3 feet at least on that side.
Pool equipment... also racking my brains on this one. Ideally would like it in a small structure so the cabana would be great, but would have to deal with long runs. Having it on the other side of the yard would mean a shorter run, but the need for another structure, which I would rather avoid.
Skimmer... good point. Thanks.