Re: The Chicken or the Eggs?
Welcome to the world of sailing. What's the chance of befriending another sailor/boater and putting in time on OP's boats while you are saving and planning for your own ?
My college roommate introduced me to sailing, many years ago and I sailed with him on his boats for years, before I finally purchased my own. At times, when I was in between boats; once it was as long as 10 years. I probably sailed more on other peoples boats; Racing in club races one night a week, daysailing on weekends on another boat, long distance cruising as Mate/ crew at other times on another. In many ways, it was the best of all worlds. I got to sail a variety of boats and had little or no expense or worries of ownership, other than some occasional sweat equity; and I learned from a number of sources, soaking everything in.
The Coast Guard will require you to document your time, and there is a recency requirement, usually 90 days in the last three years. So, if you do spend time on other peoples boats, you want to get them to sign off for you on the coast guard's time sheet. Obtaining and documenting the sea time is often the most difficult part of obtaining the license.
In the off time, I read everything I could get my hands on regarding boating and sailing. The technical stuff can get a little tiring at times, and then you can pick up the great stories and accounts. Joshua Slocum, Chichester, Dana. And newer titles like Fatal Storm, At the Mercy of the Sea, Close to the Wind.
The middle of winter, when the ground is covered in snow, is a great time to take a course or read a good book to keep the passion alive, and bide the time until you're out there sailing on your own vessel.
Good luck on your journey..