Steady Hand's $30k & Under "finds" thread is a great one. Though on your budget
it's going to be tough. Look on sailboatlistings.com & craigslist
Also spend some serious time walking the docks, & if you see something that strikes your fancy, get in touch with the owner. Through the marina, & or via leaving a note inside of a weighted ziploc bag. Try Write-In-The-Rain paper, it's waterproof.
Especially if she looks as if she's not been used in a while. You can do the same in boatyards
. I know a guy that got a Ranger
37 for $1k that way. She needed new rigging
& such, but still...
For that kind of coin, I'd concentrate on the S. end of the Sound, & up towards Anacortes, etc. And over on the Peninsula(s). Places that are far enough off of the beaten track that boats which are for sale
get less interest due to location, & thus sell for less.
It couldn't hurt to look north of the border too, given the exchange rate. Greater BC, Van. Island, Naniamo... You see smokin deals in those areas regularly.