Hmmm. Well, since progression is key to everything, it would make more sense to me to (in the case of diving rolls, for example) jump empty air space or soft, inanimate objects first to strive for distance until point of diminished returns is reached. There are most certainly other ways to measure distance and progression without injury. Then just repeated training, ki training and conditioning (I'm not a great jumper, btw) will lend more distance and ability over time and practice.
One also must expect that when one reaches one's limit that injuries will occur. I'd rather dislocate, sprain or break something rolling or falling farther than I've trained than rip an artery or organ open, or skid on my skull for 20 feet. I hope to say with training, one would be more able to take a fall than without, yes.
Let me make something perfectly clear - I don't like to fall. I did it a lot incorrectly as a kid. Come my BB test I was just as nervous about falling for my partners as about the rest of my test. My guys were very kind and didn't make me do any joint-lock throws, just all judo throws, and I can handle those better. I have my own little mental block about it (I think it has to do with injuring someone on a throw like that). But my interest in training for this is renewed lately, inspired by my daughter who did her first flip fall from a gooseneck jointlock the other night and did great!!! She was so nervous.
Whoops! off topic.