Multiple bags, multiple strategies
In addition to Michael's baggage management strategies, I have my own additions and variants:
Instead of a photo vest, I use a jacket from Scott eVest
Scott eVest . Scott eVest was originally just a maker of vests, but they've added jackets and other clothing. I use a full-size jacket with zip-out fleece liner from Scott with a huge number of pockets; sleeves zip off to convert jacket to a vest. It attracts less attention than a photographer's vest. I have even carried a wide-screen laptop in the large pocket across the back of the jacket onto a tiny puddle-jumper plane with no carry-on space with nobody noticing. I just have to be careful not to sit on the laptop.
If you put your tripod in your checked baggage, be sure to put the tripod head in your carry-on. If the airline loses your checked bag, tripod legs are easier to replace from a local camera shop than your favorite tripod head with Arca-Swiss mounts and clamps.
If the hard-sided Pelican case or hard-framed rolling bag weighs a lot when empty like the ThinkTank Intl, use it to check clothing and non-critical gear into the luggage compartment instead of carryon, and carry on your important gear in a soft, light weight bag (like a Moose Peterson bag) to save the carry-on weight allowance for gear. Then when you arrive at the destination airport, swap the camera gear back into the hard/rolling case for local transport/storage.
You could also just use a lightweight Moose Peterson soft-side bag
Moose Peterson Bags and roll it on one of those collapsing/folding luggage wheel carts and pack the cart into your checked baggage when your arrive at the airport.
