Removing a 300 by hand would be very difficult. I have a tire machine and have changed 330/30 car tires and found it is easier to break the bead with the changer and then cut the tire off. Going on is easy. One of the problems I can see having without a tire machine would be not being able to hold the wheel down with the forces needed.
I have a new 300 to put on mine so I will have this experience personally very shortly.