Just got my Tristar in Navy/Iberican and am very pleased with what I see so far. Craftsmanship and materials live up to everything I've read online. I'm a professional photographer and typically travel in 3-5 day bursts. My usual carry-on is a rolling ThinkTank camera case and I may stuff some clothes in a Filson tote if it's a short trip or will check in a small 20" rollaboard suitcase if it's an extended trip. However, I'm hoping that with the Tristar, I can get away with carrying it on as my personal item since it appears that the Tristar fits under most seats.
Has anyone had experience in having the Tristar as a personal item and having a second (larger) carry-on bag? I typically fly United and the Tristar technically is larger than the personal item size specs (United: 10x17x9" / Tristar: 13x19x8"), but curious if most gate agents overlook the bag if it's handheld vs rolling.