How I pack has a lot to do with the resort I am going to. My last trip was to snowbird, so I didn't need a boot bag at the area. I took two roller suitcases, one of which had the boots in it, and a non-wheeled ski bag. I couldn't use the third set of rollers anyway, because I had onehand for each roller suitcase. I also had a backpack with my laptop in it. I hooked the laptop to one of the roller bagts to move through the airport, slung the ski bag over a shoulder and rolled the two suitcases.
If I needed a boot bag at the area I would either take a small boot bag to carry on, so it would not be wheeled, most likely a back pack, or I would take my mammoth roller boot bag, which I bought at Costco. It also has back straps which were very useful in snowy parking lots. Most of my skiing was done at areas in the East, to which I drove. If I had a small backpakck for my boots, then I would want a roller bag for the skis. Otherwise I have two hands pulling rollers, so no way to handle a roller ski bag.