Eric,
I use a Lowe Pro / Pro-Roller 1 which works pretty well. It fits in the overhead compartment of the airplanes and has never given me a problem. It is going to be snug to fit all that equipment, but I think it will work... No UW-housing though :-)
It is at least worth to check it out.

When I do not use it for photo/video equipment I have used it fto fly with essential dive gear (3 regulators, 40 or 60lbs wing, wetnotes, Bottomtimer, Compass, 13.5 A/18w HID light, 2 backup lights, charger, 2 masks, etc.) When I use it for Dive gear I remove the photo-insert, and use the wing for "padding", which gives me a little more room. As you can see, it has room for quite a bit of gear.
Anders