You can't tack upwind with Outleader kites, these are the ones which were(and are?) briefly used in (conventional)sailing and somehow recognized by the ISAF(?).He can't tack upwind with a kite. It is a down wind sail.
You might want to change that block to one with a swivel in it, so that line runs freely and not chafing.
I can tack up to about 60deg off the true wind, see my previous post for some more details.Yes, I can see how that works when reaching. I assume you can't run with that so you probably do broad runs. How well can you tack into the wind?