I have always traveled with one carry-on bag so the current airline fee changes only mean I will have less space in the overhead compartment, due to more other people using it, the next time I fly.
The main advice I can give to anyone trying to fit everything into an overhead compartment bag is (1) buy the cheapest bag you can get in Chinatown because it will be light. When it wears out get a new one. Four light cheapie replacements will pay for one heavy expensive one.
(2) Wear your biggest-heaviest shoes, pack your light ones. The same thing with coats, sweaters and jackets.
(3) Figure out how to get clothes washed where you are going so you take only a few days worth.