The bigger your bag, the more likely it is that they will not let you carry it on, sometimes at the gate even if it is within legal limits. We just bite the bullet and check our carry-on sized bags, and just have smaller flight bags with all our meds, anything of value (camera, electronics), everything we need for the flight (snacks, eye mask, earplugs, inflatable neck pillow etc.) and what we would need for overnight if our bag doesn't arrive when we do. (toothbrushes, change of underwear, clean shirts). We pack very light, but always seem to have our main bags that weigh 25#s. It isn't that big a deal to wait a few minutes for your bag, especially if you have to go through customs & immigration, when they are really efficient at getting your bags to you. For me, dragging bags through an airport, onto a plane and hoisting it into a baggage compartment for each flight is just not worth it. Next trip, I will check it at our home airport, fly to Seattle, Boston, Frankfurt and Barcelona, and have only a brief visit with our bags in Frankfurt when we are admitted to the EU. That works for us!
Just my two cents worth.