Re: Any tips for shooting from a Cessna plane?

It seams to me that successfully making the shot as described would be close to impossible. . . even under the most experienced hands. 1) Under a slow-flite configuration (full flaps, hanging on the prop, battling a wind currents, aircraft stability) the air speed will be too high to have any controlled dramatic flow to the scene. 2) The wing strut on a Cessna high wing airplane will be right in the middle of your view. You will have a highly restricted area through which to shoot. 3) A 70mm focal length lens would be virtually impossible to hold steady. 4) Repeat takes won't improve the situation.

Suggestion: Hire a helicopter with a gyro door mount for a repeatable, stable platform. Or a long crane, use a wide angle lens, swing and boom down to your tight shot.

You have outlining a complex and difficult shot. I doubt that you will be able to find a pilot who is interested in attempting the low level maneuver that would be required, plus the shooting obstacles are most difficult to deal with.
Good luck,
Ken