There really isn’t room for much of any sort of bag in the overhead. I usually bring a soft sided gym bag that fits under the seat to carry anything I don’t want out of my control and at times I am able to fit it in the overhead. You will hand over your bag as you board the flight and get it as you come off the plane so not much danger of the bag missing the flight. You will then have the bag in hand and be able to take on board for the second flight. The bags normally appear. quickly so not much of a wait. Just remember to wait on the jetway for them to come up. In summary I wouldn’t change anything minus perhaps carrying on a tote or gym bag if you have items you are worried about but in 100s of flights I have never had any issues