The tiller is so long that you can not pass in front... it would hit you, crew, shrouds. You have to swing it aft. You will get used to it. Face aft when tacking and pass from one hand to the other or simply toss into the water and drag it until you are set on the other side. You can steer holding the tiller crossbar.
Trim is tighter as you head closer to the wind. Looser as you bear away. Light or heavy wind is pretty much the same. Difference is in hiking or trapeze to get you weight over the side as the wind increases.
Use the tell tails for proper adjustments. there are a few FAQs on the topic.
FAQ section: http://www.hobiecat.com/forums/viewforum.php?f=18
Sailing FAQ: http://www.hobiecat.com/articles/basics-sailing,182/