I shopped with my daughter and son-in-law for their first boat in the Puget Sound area last summer. They had a similar price range. We sifted through a lot of chafe before finding a reasonably maintained little cruiser.
Reaslistically, you'll probably end up buying two boats. The first one to make all your mistakes in while sailing locally, the second one when you have a better idea what you like and dislike.
1983 Fraser 41
La Conner, WA
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Boating for over 25 years, some of them successfully.