I know we’re still a little ways out, but has anyone talked about possible takeoff times?
That depends upon the route taken. If we go by trail / road then it's 5 hours minimum so departing at 9AM gets us there about 2pm.
If the scenic backroads are taken (legal and 95% asphalt) it's about 2 hours one way at 25 mph. So leaving at 10AM puts us there about noon.
I have done it both ways several times. Generally after going by trail and eating at the prison already 7 hours have passed and people are ready to go back quickly which I have run them by backroads. Going in this manner it is typically a 9AM to 6PM ride covering 110 miles round trip from RRB.