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1. The recent breaking crossbar video was a bit freaky. What are some symptoms that something might be out of adjustment?
Breaking a crossbar is very uncommon. I would not be too concerned. Inspect parts regularly before sailing.
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2. With the boat in the water, mast stepped and jib bent on, how soft or tensioned should the shrouds be?
With jib hoisted... shrouds should be taut. When sailing the mast will rotate and bend, so the rig loosens. Some slack in the lee shroud is expected.
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3. I am not very clued in on proper angles on the pivoting mast. When sailing close-hauled, and the main sheeted in hard, the mast seems to be rotated hard to leeward. Is this wrong? Am I oversheeted? Am I pinching too high? What am I looking for with regard to mast rotation and sail trim?
On a 16, the mast rotates to the stops on all tacks. Mast base and step castings can be worn, so replacement can help prevent over rotation.
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4. When trying to point high in light/medium air, where should the jib cars be set? I have them set as close to "inside" as possible. Is that wrong?
All the way inboard. Only time they ever move out when sailing up wind is in very windy conditions.
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5. There is some weather helm when sailing close hauled, but I'm unsure if it's excessive. I can maintain course and holding the tiller extension isn't causing undue fatigue. Any sail trim or equipment adjustments I should check for this?
The rudders may not be staying locked down or the rake angle needs to be changed to match the mast rake. There is a detailed FAQ on rudders here:
https://www.hobie.com/forums/viewtopic.php?f=18&t=467