Darren,
I went through this evaluation last year as a newbie sailor.
The best advice I received was to get involved with a local Hobie Fleet, which I have done. The people in Fleet 23 here in Dallas have been extremely helpful. They have been teaching me how to sail and supporting me along the way. Sounds like you are already taking the right steps.
Regarding the boat to select, I decided between an H16, a Wave and a Gateway. Ultimately me decision was driven by budget. Wave's and Gateway's are very nice and I would have been pleased to have either one. However they are typically not available used in the DFW area (or it seems like any other area of the country) at anything substantially less than the retail price. Since I didn't have the budget to buy new i purchased an H16, which are easy to buy used at a reasonable price.
Initially the H16 was more boat than I was ready for. However with help from Fleet 23 and lots of studying I'm getting better. I have capsized twice, but hopefully I learn from them and I'll be less likely to do so again! The key is to be sure that I am sailing in conditions I can handle. I wasn't doing that when I capsized.
Another bit of advice i received from a post on this site is that I would grow into an H16 and out of a Wave. So depending on what you want to do with your sailing in the future keep that in mind. If you ultimately want to race or experience more extreme sailing then an H16 is a better choice. If you are happy with cruising around a lake or in the ocean without the need for extreme then the Wave is a great boat.
Whatever you choose, I'm sure you will have as much fun as I am having!
_________________ Michael
'86 H16 #91487
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