Regarding the medical for the PIC. You are able to go in and created a sub item for the medical. This way when the 6 month PIC medical (over 40) expires you will see the sub item that is still current. The pilots can be added as SIC to a 135 trip or a 91 trip that does not require the first class medical every 6 months.

See the screen shots below showing how he set up the sub item.