I travel with 2 carry on bags on my photography trips and often go into small regional airports. I never had a problem fitting any of my bags into overhead bins and technically one of my bags is slightly over allowed size but its soft and when not full I can fit it.

If you dont have any valuables or fragile items you can gate check it if it will not fit into overhead bin. If flight has empty seats you can try convincing FA into putting your bag into one of the seats. Few years ago when I wasn't EXP this was done to me by FA after I explained I had over $10k of fragile stuff.