I started experimenting with different insertion methods using a mirror. Surprisingly helps. Best method was to detach the cable from the IEM and just try a bunch of different "screw" approaches without worrying about the ear hook or connector. Based on these experiments, I'm guessing that the fundamental issue I'm having with the Meteor is a combination of a shallow fit and the slightly upturned nozzle. Angle matters a lot more than I would have guessed.
Still not a great fit, but it is better. And it's much more comfortable. I'm hoping better fitting tips will get me the rest of the way. Thanks for the suggestion.
Cool.
The spacer trick above might help also.
I do that with my IE600 to help with the shallow fit. Even just pushing the tip out along the nozzle by a couple of millimeters makes a surprising difference.
I cut spacers from the stem of some tips that were to small for me.