C.M.
At 8 mos., it will be a LOT easier now than later on! Curb check your luggage and the car seat. Bring the stroller with you. You can hand it to security for screening and then gate-check it at the last moment. It will be waiting for you when you get off the plane, so you'll have immediate access to it.
My guys don't fight their naps, so I usually try to schedule a flight with a take-off time close to their usual nap. Take-off and landing can be rough on little ears, so I make sure to have bottles prepped - the sucking helps ease the pressure. Security usually makes a big deal about checking bottles, but TSA guidelines have an exception to the "no fluids" rule that allows you to bring a reasonable amount of breast milk or formula through security for an infant.
I've never used a hand pump, so I'll let others comment on whether to bring the big guns along.