I did exactly what you are saying. I bought a H16 my last semester in college with my tuition money. I read a few books, then got on the water and had a blast. 10 years later I own a Pearson 30. Pirorities changed so I had to adapt my sailing to fit. Good thing the wife loves it. In between I sailed 70' wooden schooners. I found the most valuable lesson the Hobies have taught me is to think ahead of the boat. They sail fast and things happen fast. Once you get used to it and are ahead of the boat, you become very comfortable and confident. To get every ounce of speed out of a Hobie you still have to know how to properly trim sails. Understanding your boats strengths and weaknesses is critical. Hobies can be very unforgiving. On the other hand if you make a mistake chances are you will get wet and have a great story to tell later. Also the simplicity of the rig and the boat allow you to just sail.
Transitioning to a larger mono has a few things to look for. Search this forum and you will see the advice offered.
I say go for it. You will have a great introduction to sailing, have the time of your life, and all for only a around $1000.
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Last edited by nickmerc; 08-18-2011 at 06:51 AM.