Normally the first year a tree is planted, most of the work is going on underground. As long as it lived and stayed green you should be happy. This year it should put on some more growth and the third year it should really leap. I'm no help w/ the second question. I remove mine after the first year, but I guess it depends on the situation.

Not seeing how major pruning by a contractor every so many years into perpetuity is an economical choice. And if you have turned them into pollards or otherwise severely pruned specimens then the charm of the natural shapes has already been lost - maybe plant some more suitable kinds of trees among them, cut the olive trees out after the new set is of some size. Otherwise they should probably be trimmed frequently, maintained as formal specimens instead of getting whacked back hard at longer intervals. Every time they are forced to regrow most of the top that was present at the time they are drawing on nutrient reserves in the trunks and may be gradually becoming diminished by the repeated assaults. There is also the possibility of trunk decay developing due to the large pruning cuts being made. For planting near swimming pools you want plants with large parts that do not get sucked past filters. As you have described olive trees are probably about as bad a choice as one could come up with.

I'm pretty lazy about drying herbs. I just pick them, tie them up in a shady place (my kitchen) and hang them from something until they're dried. Sometimes they get a bit dusty because I'm a major procrastinator too. Native Americans would just tie their herbs up in their abodes for the winter or so I've heard. I've also heard that the best times to pick herbs are early in the day once the dew has dried from the leaves. Then once they are dried enough I just put them in a clean glass jar and put the lid on. I've heard that a good way to save basil (depending on what you want to do with it) is to get fresh basil, throw it in the food processor with some olive oil (IF you are making pesto or want to cook with it) and freeze it in ice-cube trays. Then you can make pesto or add it to spaghetti/pizza sauce whenever you want it. Thyme, oregano, rosemary are hardier herbs and I just put them dried into a glass jar. Keep the leaves whole if possible as when they get crumbled they usually lose their essential oils faster. Keep them in the dark if possible to prolong 'shelf life'. Most herbs eventually lose their zing except for laurel, or bay leaf, they're supposed to get stronger in storage.

Thinking on this but my first thought is not to do black cabinets. And, don't worry about "floor fatigue" so much. It's not like you'll be standing for hours in a kitchen like a restaurant chef. I have porcelain wood look tile and I don't notice the "fatigue" of a hard floor. It always looks best to have the flooring the same throughout so nix the idea of changing the flooring from the living space/kitchen space. The floor plan you show is too small to see details. I'm thinking if you are going concrete floor, mix the cabinets with natural wood look and a light counter...maybe a white quartz.