OK - here is what I have discovered trying to get an automated pilot to fly different routes on different days: That theory simply does not work due to the way the system looks at scheduled legs.
Example: I set up 4 legs for Wednesday only, 4 different legs for Thursday, Friday, Saturday, Sunday.
The system starts at the top leg and when the pilot is done for the day, it will revert back to the top. The system will not "look for other flights" if there is no flight on the given day in the top leg.
This does not necessarily need fixing, one just has to recognize the limits of the system. All flights in a schedule must be on the same days. Pilots can only be assigned one schedule at any given time as well. So you cannot assign a pilot Schedule A for Wednesday and Schedule B for Th, Fr, Sat, Sun giving the pilot 2 days off in a row weekly.
Now if you want to keep an aircraft flying for max profit, you can have Pilot A fly it in the mornings on MTWT and Pilot B fly it in the afternoon evenings on MTWT, then Pilot C fly it on FSS. Each pilot would fly their own schedule as Pilot C would need more flight hours per day only flying 3 days a week.
I am finding it easier just to have some dedicated down time for both pilot and airplane so when the airplane needs a 24 hour A check, one can simply do it on the pilots' days off.
For super long flights, I have 3 767-300's that fly Detroit to Honolulu, Las Vegas to Tokyo and Las Vegas to London. I also have two cross country pilots who fly 737-800's from Las Vegas to Detroit and Las Vegas to New York. All of those are being dispatched daily with "book flight" and not on a multi leg schedule. When they hit the mark close to 100 hours, I simply don't book them until their logbook clears a bit and they get many days off in a row at home. This also kicks in the hotel expenses as designed because after such long flights with the 767's, they need at least 24 hours off to be well rested to fly back (just my opinion to keep things simple).
The math involved trying to figure out the exact routing to keep pilots up in hours without going over is quite complicated and those who do not like to crunch the numbers can always just book their pilots on a daily basis without trying to make a schedule work to perfection. The other solution is to overbook them for hours per 28 days and when they get close to 100, just remove the schedule until the hours start to go down in their logbook and then reassign the schedule again.
Either way, Automated pilots are not a maintenance free feature if one is looking for less hassle than dealing with humans.
Also, the airplanes are flying far more than they would be with humans who have real lives to attend to other than playing video games, so one has to keep a close eye on the aircraft status as well and keep them serviced. My CRJ's with all the short legs are now getting A Checks about every 30 days or so.
The Automated Pilots option is a fascinating feature if one is looking for more "management" than just flying. Be advised however that one has to have the time to burn to experiment and play with the automated pilot option, it is not something one can just plug in with a few minutes work and then leave it to make you money. It is a "hands on" management option.
..This year or next year??