Have you tried this website, to simulate the shadows?
http://shadowcalculator.eu/
(works outside EU to)
I explained how to use it in this topic
If you select the hight before placing points, they already all have that hight.
I would also consider placinbg earlier ripening fruits/varieties in the spots that get full sun mid summer but some shade from sep on.
I would also shy away from known biennial bearers. (flower development is mainly end of summer.)
Although the extra shade during flower bud development might also lessen the flower buds to an extent that you have less biennial bearing. I just don’t know. Might be worth an experiment 