589107 - Issue with a member that has dual officer roles

Every officer position is listed as Position – Name, whether or not the seat is filled. An officer holding two positions is named beside each one, and ticking either box grants the access once.

Quote above from the Access Settings module. That's the intended behavior as access settings are listed by officer role so a person holding two officer roles will be automatically checked on both roles, regardless of which one is selected.

It still allows three separate people to have access to the various admin modules.

Can you expand on how it increases difficulty managing granular access permissions?

Drop the junior role and assign the function. Ie. drop secretary and assign the file upload function.
Also Have ALL your members read out loud the toastmasters promise and then ask for volunteers for the junior roles.