If you haven't bought the item yet, and you're leaning toward a trolley, see if you can find one with wheels that are as large as possible and with as wide a base as possible--that helps it roll if the surface is bumpy.

I haven't been anywhere in Japan where I couldn't roll-drag a suitcase with wheels. Even on mountains, the paths are usually kind of flat and packed down.

But like LapLap says, takkyubin is great--you just have to get used to the idea of traveling being so easy!