Hi Drew,
Some great images.
If you are having trouble getting the lower leach telltales to fly then I suspect your foot is too loose. Your last image seems to confirm this.
The Irwin sail is very sensitive to foot tension. I have my outhaul fully tensioned then just backed off a little for the upwind work so it doesn't flap against the boom. It will definitely improve the airflow and will prevent it from being too powerful.
As for the Nacra 16sq, it is probably very difficult to match for upwind pointing.
The lack of a boom seems to have a major effect.
Regards,
Peter