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Having sailed only a "handful" of times, there will be a large learning curve sailing the Hobie 18. Not saying you can't or shouldn't do it but I highly recommend you take out an experienced beachcat sailor your first several (if not many) times.
Here is my two cents;
The above is true of any catamaran and does not single out the 18. I sailed/raced Lightning one-design monohull for 3 years as crew back in the early 80's. I crewed on a few catamaran back in those days, Hobie 18 and Tornado. I think I took the helm 10 times total. I then committed to windsurfing and did this from 1980 to present. I wanted to teach my kids, wife and father the thrill of sailing fast. I decided to purchase a 21SE as it will carry 4-6 adults easily, has wings (biggest plus) and is one of the fastest Hobies out there. Best boat purchase ever.
It carries 6 people no problem. The only problem is I cannot solo and really preferably have 3 people on board. The upside, I can carry 6 and can still catch virtually every catamaran on the lake (to date). Maybe if the winds are blowing above 20 I might be challenged to hold the boat down and other catamarans may find an edge, but in those winds I usually just downhaul and am able to control my speed and survive.
If you are really going to sail with crew more often than not, get the 18. If you want to solo be cautious of the 18 and look at 17 or 16, but dont rule the 18 out. Purchase and learn how to sail a cat. Make sure mast is sealed and/or put a Hobie Bob on the mast to not turtle if you flip.
Have fun! I am sure there are a few on this forum who will be glad to come to Hawaii to help you learn how to rig the boat and teach you to sail.