Time & Holiday Schedules and How They Interact with Call Forwarding Selective Rules

Currently for our main hunt group, we have a "Business Hours" rule tied to our business hours schedule and an "After Hours" Rule with the time schedule set to "All day every day". I tried adding a new rule  tied to a new time schedule (outside of the "Business Hours" schedule for testing purposes) but it did not work. When I changed the "After Hours" Rule and assigned a new "After Hours" time schedule rather than having it as "All day every day" the new rule then took effect. To make sure our phones operate in the same way they did before while still being able to utilize new rules for intermittent schedule changes, what is the best way to have my time schedules set up? If I have the "After Hours" time schedule set weekly (M-F) from 5pm to 8am, will that cover all hours outside the "Business Hours" schedule (8am-5pm)? I'm worried about it not properly feeding after midnight. 

Short term goal is I need to be able to have our phones operating as normal in the morning, roll to a special rule/automated attendant for the afternoon, but go back to "normal" automated attendant after hours without having to go in each time and make manual changes. 

Also, our holiday schedule set up has never worked. We have to manually change the "Business Hours" schedule since the Holiday Schedule doesn't override it like it is supposed. Could that be because of the "All day every day" time as well? What's the best way to have Holidays set up so they work properly?

Long term goal is to ensure our schedules are set up to be as easy to manage as possible, which would preferably be automated as much as it can be.