OP - Don't let people make more of this than it is. Simply a matter of basic engineering and how to fit one item (a bag) inside another (an OH).
Gate-checking is not the same as checking your bag at the counter/curbside. You leave your bag as you enter the aircraft (whether on a jetway or via air stairs) and you get it back at roughly the same type of locating as you arrive.
I would suggest having a small bag which holds medications & valuables such as jewelry. That comes out of your larger carry-on and stays with you in the cabin. While losses on valet-checked bags are uncommon, they do happen.