In article , David Rind
wrote:
1) What do people like to use for flight planning for something
like this? Laying multiple sectionals on the floor next to each
other seems a bit painful. Is Aeroplanner a good choice? If so,
is the basic Aeroplanner the right level for this kind of thing?

Get a set of WAC charts or IFR charts.
Use DUATs and flightplan your IFR route for the entire route.
Let DUATs perform the headwind/tailwind calculation and print the
flight times for each waypoint. Once you know the time to each fix you
can determine where your two-hour stops will be.