I agree with everything you said. Watched another forum member, bwringer, do my front tire and it is clear that technique is the issue. I just haven't figured out the technique.
Have proper motorcycle tire irons, lubed everything and tried very hard to keep the tire in the deep part of the rim.
Would love to figure it out, but time is short now that the semester has started and I'd like to ride it at least a bit this summer. Local-ish to Cycle-Recycle II in Indy and they'll mount them for $12. Seems worth it at this point.