Find other Hobie sailors, on the beach, at the local sailing clubs, whatever. Buy them a few beers, and offer to crew. Ask questions, and explore what's best for you. That's how most of us learn, and when we know something, we're happy to pass it on, 'cos we all 'share the wind.'
Offshore sailing can be fun, also challenging. H16 will get you anywhere, anytime. Check out pictures and reports of the recent Hobie 16 Worlds held in South Africa. Often races were cancelled due to 40 knot winds, but everyone made it back to the beach, well, more or less.
Once you move up to larger and more complex boats, the price, the maintenance, and the skill requirements rise dramatically. It is unlikely that you can sail a Tiger alone. Even when I go out on my H18, (and I have often sailed solo,) I always make sure there are others around as there is no way one person my age can right a H18. I used to, 12 years ago, but no longer are the percentages of risk/reward on my side.
If you are a solo sailor, my suggestion is that you look around for a H17, and get yourself an EPIRB.
1989 Hobie SX18 Sail # 1947 "In Theory..."
'Only two things are infinite, the universe, and human stupidity. But I'm not sure about the former.'