Complicated lookup series for strategic planning / scheduling Help please :)

https://docs.google.com/spreadsheets/d/1fjjnwH1QEvPShlitY1XbxgCFCSxa4D2RXVWNNPA9uNE/edit?usp=sharing

Trying to automate a practice plan for a season where i can allocate my time on this page and then based on selecting the date have it autopopulate daily practice schedules - I am not sure if it can be practicably done in Excel - I am decent with lookups, but this looks to me like maybe i need AI or VB? Any help greatly appreciated - first time using reddit so apologies if I am not following decorum. Cheers!