I was in this exact same dilemma, for which I started
this thread. Of course, what I meant to ask in that thread was: what is the *largest* rolling bag that will fit in the overhead bin.
I can state without doubt that the
Briggs & Riley rolling tote will fit in any regional jet in the overhead, and that it is also the largest rolling bag that will fit. You have to put it in the overhead wheels out, but it will slip right in there. There isn't even another half inch to spare, so this is the bag you want.
Also, I have *never* been asked to gate check it. What I end up doing is when it comes time to board, I just retract the handle and pick it up. As I'm walking past the GA, it looks smaller than a lot of the purses and shoulder bags that other people are lugging around me.
Finally, I also hear you regarding your desire to become a "one-bagger". I too would love to achieve that goal, but that one bag just gets too heavy, and the joints get to creaky to make it doable. My solution is this: I have a
Tom Bihn Tristar, and the
Briggs & Riley rolling tote. The Tristar sits right on top of the B&R, and I can roll to my hearts content. When I get to the gate, I put the Tristar on my back, backpack style, and carry the B&R by the handle. I've only got to carry them about 20 feet that way, til I get past the gate agent.
Some things worth pointing out: you can pack a breathtaking amount of stuff into a Tristar. It's just so well organized, and the lack of wheels gains you a surprising amount of extra packing room, which is hard to really appreciate until you start loading the thing. Which can thus start to get a bit heavy. That's why I love just putting it on top of the B&R to roll. And I can also confirm that the Tristar, even fully loaded (and even bulging at the seams a bit, I'm ashamed to admit) will fit into ANY overhead. Thus, both bags fit into the overhead if space allows, and either will fit at my feet if necessary. Have never been asked to gate check either one (and as a DM, I do fly a bit).
Finally, I often use this
Bag Bungee to secure the Tristar onto my B&R rolling tote. Click on the Bag Bungee video link below the "See how it works" line to see a short video on how it works.
Whew. I have GOT to get a life!