Things like varying overtime rates depending on time of day, accumulated hours, whether it's a holiday, different rates for depending on specific work assignments, etc. It's not as simple as a flat rate x number of hours. But it's nothing that hasn't been done before, either.
Agreed. You also have to think about who can approve the hours booked. So you would need to have some sort of hook into the HR / Org database which determines each users entitlements. It gets very very complicated! Technically, the problem is nothing new. The difficulty lies in designing the system and getting it to work correctly with an organizations existing business processes and systems.