Thanks for the tips. We did sit on the leeward side and get the windward hull out of the water. That's particularly important to get the sails to drape correctly. The mainsheet was nearly two blocked so I think the mast rake was as much as there could be. Shrouds could have been looser, I suppose. Battens might have been too tight, though, since they didn't pop over on tacks without some work from below-but main had a decent shape...traveler and mainsheet were amidships. The jib and main weren't quite set correctly together. With main telltales perfect, the jib was luffing slightly. Didn't want to oversheet either sail, though in that light breeze. Tack angles seemed to be 110 or more. I wanted to drag the boom to weather, but traveler doesn't work that way (and no boom). Next time I'll bring a little spare line to haul the main clew to weather and get some better twist at the top of the mainsail. Disappointing, but that's not too surprising for a boat that's new to me. A lot of the fun in boats is learning their quirks--had similar issues with the other boats I owned when they were new to me. I tend to get rid of them once all the surprises are gone.
If you have not done it yet, add leech ribbons to help set twist. One above the head of the jib (about inline with the bottom of the Hobie H logo on my sail) One at the same ht as the jib head (about the middle of the big "O" in Hobie) and one about equal distance lower (about the middle od the "I"). It is easy to oversheet the main and stall the upper leech in light air.
I don't think you will find any improvement by pulling the clew to windward. The boat needs speed to go upwind and going for center line boom trim as you would in other boats might allow the boat to sail closer to the apparent wind the VMG and COG will be worse.
I cannot say this often enough. You must have speed before point. With the same jib trim (windward tell just flicking up 50% of the time) and the upper leech ribbon flicking behind the sail 50% of the time I get about 30° apparent out of the boat. This can be 60° off the true wind slow with huge leeway or less than 55° off the true wind with good speed and much less leeway. The sail trim looks identical. The Hobie 16's are getting to 50° off the true wind and I'm using them as a target for upwind VMG.
I use RaceQs on my smart phone to log sailing sessions for review. It is free and a great tool to grade your steering and tacks as well as your sailing angles over the ground. Still early days for me too, but my goal is to beat a H16 in the next two weeks. I think that in 12+ I can do it. Tough in 8-10.
BTW - my sail maker found a hard spot in the jib where the production guys missed a match-up mark in one seam. He thinks it was the cause of leech flutter. Should have the sail back today or tomorrow so I can race Saturday.