sureshot, in my opinion for what it's worth, it's less the raw number value of energy so much as it is tissue destruction. Sure, higher energy commonly means more tissue destruction, but that's as much a function of bullet design as anything else. That is, a .505 Gibbs solid has a lot more energy than my .243, but the bullet won't tear up much tissue.
My 85-grain .243 bullet makes a double-handful of mush of a deer's heart/lungs. But, so does my '06 with 150-grain bullets--plus an exit wound.
Back to the thread: The best comment, so far, has to do with twist and bullet weight, for the .22-250. Again, shot placement with marginal bullets is far more important than with larger bullets, larger weights and bigger diameter holes of exit wounds. Further, an angling shot is, IMO, pretty much a no-no with the lesser cartridges. Penetration is also important, and no .22 is going to do that well. (Neither is my pet 85-grain .243 load, either.)
Maybe think of it this way: I've no fear of taking a shot on a running deer with my '06. I won't do that with my .243. A less-than-perfect hit with the '06 will likely put the deer down, and a second shot will finish the job. BTDT.