Touring questions are on topic, however this question does not really pertain to the music side of touring. Here is an excerpt from your second paragraph:
The trouble is, there are many different ways to get from point A to point B and I need to find a way to solve the problem of optimizing the route that I take that keeps the band playing the most nights, pays the most and also reduces our travel time.
The only part of this that involves music is that a band is touring from point A to B. This problem is a travel logistics problem and can be seen with anyone who needs to travel to many places especially for business.
This is an important topic and I understand why you would ask the question, it is just at it's core more about travel logistics then music. There are other SE's that may be able to help you with travel logistics like Travel.SE (I found a similar question on it).