So the solution to Point 1 is to load the car in ODO, and point 2 is for ODO to be somewhat dynamic - upon stop complete it reruns the solution for remaining stops. The trick to this is, the solution in point 2 will have to be pretty close to the original one or the driver will STILL be searching for packages out of sequence order, or, the driver simply has to live with the original ODO.
The bottom line is the ability to run a route correctly needs to be socialized across the company and not solely in the head of one or two individuals. Also, as you add services and delivery customization, the routes will become more complex, change on a daily basis, and the routines good drivers use won't apply anyway.
The company will have to gamble that the money they spend in the transition will be worth everyone's time when (if) the solution works like it's supposed to and revenue continues to rise.
One thing we know we can't do, is just "leave everything alone" in RDO and be complacent. Other companies will eventually beat us at customization and win the business in that case.
The market is changing to where customers, right or wrong, will expect a motorcycle to come up next to an Uber they're riding in and hand their package through the open car window because they bought a Panic! at the Disco ticket and couldn't be home that day.