Join Date: Mar 2010
Location: SF - South Bay
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More advice from a guy - please forgive me....
A lady I know is in a similar position. Her strategy is to buy a smaller boat - Santana 22 - and learn all she can with it, doing all maintenance, repairs, upgrades, learning to sail solo (and with others). Make mistakes in a small, comfy environment, where the cost of mistakes - both financial and in terms of consequences - are less. She also crews on larger boats for the experience.
After 12-24 months she plans trade up to a bigger boat; perhaps directly to the 34' Blue Water boat which is her ultimate desire. By then she will know what to look for, and be ready to take it on more challenges....
This seems to me to be a good way forward.
As a starter, most local yacht clubs have informal "beer can" races. This can be a great way to build up experience, see different boats, and find people who will be willing to help make your dream a reality. You may want to try that.
Crewing on another boat will certainly teach you how to sail - but owning (skippering) your own boat has a raft of challenges that you can only truly understand when the boat is yours! It feels totally different being a crewmember than an owner. You think about many different things - and in a different way.
Good luck, and keep the dream alive.