We do not like checking our bags but that is not our main issue.
We are independent travelers. Often we find ourselves having to walk up one or two flights of stairs in a B&B, etc, dragging a roller along a few hundred metres of cobblestone streets, broken sidewalks or no sidewalks, humping them in and out of longtail boats, water taxis, trains, on to a ferry or into the back of a van or a rental.
By ourselves.
So now in our 70's we only travel with what we can each physically handle. Having one bag is not the only issue. Bag weight is an concern.. Our comfort zone is in the same area as many regional flight carry on restrictions in Europe and Asia. 7-8KG.
At retirement we were not ready for only the cruise, cruise transfer, 4-5 star hotel experience. We had experienced lots of that service level in our pre retirement life. We still do combine this type of travel in our plans.
We tried everything to reduce our bags. The most effective for us was simply to buy a carry on roller each and limit ourselves to that. Challenging for the first year, now it is the only way we would go....help or no help.
It is not something that I would recommend to everyone but it works for us. In our travels we see more and more retirees doing the same thing for the exact same reason. Physical limitations and/or independence. We did not have a choice. It was either reduce travel and/ or change where we wanted to travel and how we wanted to travel.