Be sure to check the specs for weight. Some bags will say they are light, but when you look at the specs, they are not. Bags with 4 wheels are usually heavier than those the same size with 2. Hard shell bags are usually heavier than fabric ones. Bags that have wheels and convert to a backpack also usually are heavier. I'd keep the bag weight to 6 pounds or less.
Having both fabric and hardshell, I find fabric bags better because they can be smushed around to fit where they need to go so long as they are not stuffed too full. I have a Lipault Paris 22" spinner. It's a French brand. I have never had any issues with it on even the roughest of cobblestones. I just tilt it like it had only 2 wheels. I also have an Eagle Creek 20" Load Warrior Duffle with 2 large wheels. Both are fabric.
I find the Lipault easier to push, pull and generally move around because of the 4 wheels. I find the Eagle Creek easier to lift into the overhead bins on planes, and to put on the overhead racks on trains because it has multiple handles and places you can grab it to lift it up. Lipault also has 2-wheeled bags and Eagle Creek also has spinners.
I use baggallini totes as my "personal item." The ones I own have a double zipper pocket that fits over the double rod extension handle when both zippers are unzipped. Note that these do not work on single rod T-shaped extension handles.
Take a metal measuring tape with you when you shop in person to check the measurement from the floor to the top of the extension handle. As others have said, the specs often do not include the wheels and handle. Also measure the width with it on its side and the depth with it on its back.