The Wave is a good idea. I rented one this weekend and it was very easy to sail solo. Not sure about rigging as the rental folks took care of that for me. I will say it wasn't nearly as exciting / terrifying as my 16 though.
I'll share my experience learning on a 16, for what it's worth. I jumped straight into an old, but solid 16, and it has been a great experience. I was reluctant at first, but after watching videos of these guys flying a hull at speed
, I was hooked on the idea. $1500 is about what I ended up spending on the boat plus repairs and upgrades, which seems typical for a good used 16. Biggest issue I have is just finding a person willing to crew and help with rigging, lauching, etc. Don't underestimate the importance of teamwork in sailing. I've read a lot, watched a lot of videos on youtube, but most of all sail whenever I can. After around 10 sailing excursions, I'm finally feeling pretty confident, although I've had some colossal failures along the way. This forum has been a huge help reading and asking questions.
Maybe a good stepping stone would be to take a lesson, rent, or sail with a friend. Even if you don't know someone with a Hobie, just ask here, in my experience this is a great group willing to share and teach (give me a shout if you're in AL). I say just go out there and do it, but what do I know, I'll say yes to almost anything that sounds fun.
Bradley M. Davis - YouTube Videos
'76 H16 Flamer #20060 - restored and sailing
'84 H16 Blue Hawaii #79922 - under restoration