The hot tree is Arbutus. New cultivars that need little water and have red trunks and branches- nice spring flowers in pendants. Or,go with very light shade making trees like the various Mesquites- won't interfere with the Olive trees.

The Taebulia's..always a great tree in Los Angeles. Coral tree's..smaller types. But smaller types can still get large.

There is a difference between trees that will grow in shade and those that provide shade :-) The arbutus and others mentioned are full sun trees that can cast shade but are not going to be happy growing in the year round shaded conditions the OP describes.

A few shade tolerant choices to consider are vine or Japanese maples, certain deciduous magnolias, dogwoods, western redbud, hornbeams, beech, azara, river birch, katsura and stewartia. Depending on exactly where in CA you are located, not all may work for your area. Check to see what your local independent nursery offers.

The boo and the Ficus are trimmed vertical,not spreading out. So,it's not quite the shady shade. Ficus and boo roots are going to be real competition also.

Maybe just skip putting tree's and go for shrubs there...those will never interfere with the Olives need for sun.

How about put a tree in the center to block the phone pole?

Whatever tree you put in the right corner is going to lean away from the bamboo. No harm in that, but it won’t have a regular up right tree luck.

What tree did you go with, if you moved forward?

Just curious as we recently planted a few trees and we went back and forth on it, particularly because my husband wanted some of them to be fruit. As my screen name indicates, I live in Los Angeles proper too.

I went with an eastern redbud. I also realized this summer that the corner does get some sun, so it's not 100% shaded.