Unless you sail in surf do yourself a favour and go out on any daggerboarder of 16 or over. I took an H16 freak out recently on my old Hydra (16 foot Tornado copy) and he was shocked by how benign and well behaved it was. You can just go out in stronger weather if you need to be "on the edge".
The great thing about going from H16 to say an F18 (apart from speed) is that your reactions will seem superhuman. You will need to learn a little more about sail tech and trim. Those old Hobies are strong platfroms though eh!
Outdated is kind as far as the hulls are concerned.
only opinion so don't wet yourself if you love your H16.