I have an 2008 and a 2016 Hobie AI. The '08 is lighter, has a smaller sail (7 sq. ft. less) than the '16. The '08 and '16 are competitive when sailing side by side, but like everything, there are pros and cons. The '08 is a better boat as a single hull peddle kayak, because of less weight. The '16 is a more comfortable boat in higher wind speeds, because of improved hull design and more bouyancy in the main hull and longer amas. The '06 has a longer rudder, so at higher speeds, steering is improved. The '16's peddle drive is easier to install, because it has guide pins, so it goes in straight every time. The biggest benefit of the two is that your butt in not sitting in a water puddle in the '16, because of raised and improved seating.
