Re: Sailboat under $5000 for Puget Sound
Getting the mast up on a 25' boat will take 2 or 3 people (assuming the mast step has a tabernacle). 3 is safest the first time, once you've practiced you can probably do it with 2. 1 person is not enough.
You'll also need a large truck to trailer a boat like that.
It still could be a good option to consider. Price out what it would cost to have it delivered to a yard in Seattle (I'd try Canal) and for them to step the mast. I'm guessing in total this would cost you at least $1500, but if you can get a nice boat for $1500 less then it could work out.
I don't believe that is a 1992 boat, you'd want to check other details too.
You could also investigate going up by boat. That's open ocean though and I'd want to do a lot of research before attempting it. I have no experience sailing out there.
1986 Pearson 28-2 "Elena"