Re: How big is too big for one man?
Purchase an sail the boat that suits you now. Sail, sail, sail. Grow with it.
By doing just that I learned that my sailing desires evolved as I grew. No one can tell you were it will take you.
No shortage of 22 - 30 ft boats in sail able shape from 2K to 10K. Fixing stuff and sailing around will teach you more in a season than a lifetimes worth of reading.
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'88 C&C 30 MKII