I started out on a H16 and sailed it mostly solo. After about 6 months I sold it and bought an 18' boat which I still sail mostly solo. Here in FL we don't get really heavy winds all that often. H16s are a great value for their money. Pick up a FL sailboat trader (or go to www.boattrader.com ) and see what they have in your area.

I'd recomend against putting a deadline on when you'll buy your boat. Instead put more emphasis on your experience level being at a certain point before making a purchase. When you learn how to sail a 16-18' cat by yourself and have been on enough different boats to know which will best suit your needs, your views on what you want may be very different than it is now.

My first boat purchase came down to a Hobie 16 and a G-Cat 16. I blindly chose the boat with more sail area and went with it. I bought H16 #4032 (Well, at least one hull wasn't original) and after I learned to sail pretty well I discovered that it was not what I really wanted in a boat. Had I bought the G-Cat 16 I'd still be sailing it. Sure, in the end things worked out and I'm on a G-Cat 18 now. It's a little bit big for me, but I can keep up with my friends on P18-2s and H18s who also single-hand (though they outweigh me by 40-50lbs).

The Hobie 16 is the right boat for a lot of people, but it's not for everyone. Find out what you want in a boat, and then find the boat that has those attributes.