I think the problem is that the logic of the whole thing is not intuitive. This step in particular;
5. Make a change that affects the route layer (e.g. paint the ground)
Sounds simple, but most/many people would intuitively expect that while in the Route layer, you change the date, then save the Route, the date change would naturally be included in the save. But it's not.
Instead, you have to remember to do something extra that is trivial and entirely unrelated to date (such as move an object or paint the ground) in order for the new date to be saved along with it. It's nuts.
.
T:ANE SP4 (105946), TRS19 SP5 (117009), Max 2009/2012, PhotoShop
Win10, i7 5820K, 3.3GHz, 32GB ram, GTX 980Ti 6GB, 2x512GB SSD