So, my mom is at that age where shes a little old lady. When we fly together, at this point I'm often left trying to wrangle a total of 2 rollerbags onto planes and into overheads - hers and mine, plus my personal item. She can usually handle her own personal item on boarding, but I'll usually carry it off for her, so that means I'm often wrangling 4 items off of planes when everyone is impatient, and I'm getting a little tired of the judgy looks.
Now, I can hear the advice already - Just check her bag. we do. she's always checked a full size checked bag for any trip longer than 72 hours. That has not solved the problem. Now, she flies with a fundamentally empty carry on, which she refuses to let me gate check because she wants wheels on arrival and during layovers for her personal item, while on arrival I handle her checked bag. I have enough airline status that gate checks have rarely been forced by the airline. A wheeled personal item also hasn't worked - she sees it as a too small, carry-on suitcase, and will still be supplemented by a backpack. A wheeled backpack is too heavy for regular use at our destinations after arrival. Day packs also haven't done the trick... it's now basically one of the few items in her carryon. I'm a bit at my wits end here. Yes, its light, so its not a huge issue, but I'm tired of the side-eye I get in the boarding line or when I'm trying to get both bags down the aisle.
For example of what I mean by fundamentally empty... we're going on a trip tomorrow. Her carry on suitcase has the following in it, and she considers it fully packed. ‐ 2 oranges, 2 bananas, day pack, a couple brownies.