Running wing-on-wing you won't get the tell tales flowing. Just try to keep consistent shape top to bottom. If the clew is too high you will spill air off the top of the sail. Too low and the top will be hooked in too much. I find generally in 5 to 15 knots of wind that the height the clew settles on its own is about right but different cut of sail may impact this.Not so must to get the sail higher. I set the height of the clew to keep all of the tell-tails flowing. at the sail it eased out a long way, you need to raise the clew to keep proper shape in the top of the sail.
As far as having a pole angled up, this likely happens because the boat only has a ring on the mast instead of a track and the ring isn't at the right height. The pole should be level.