Re: Sailboat under $5000 for Puget Sound
I disagree with Joy, having also done it in a smallish boat with an outboard.
A larger boat with an inboard is going to have a much more comfortable sea motion. There are places in the Salish Sea where you can find 4' waves, but with careful planning around currents and weather (easy if you have all summer for your adventure) that is rarely a concern. I like bigger boats, but you'll have to be very lucky to find a ~30' boat with an inboard that is in seaworthy condition for under $5000 in the next couple of months. Since you are on a tight budget (and I assume that includes covering any necessary immediate repairs) a smaller boat is going to be a lot simpler and easier to work on.
The smaller boat will also save you money every time you use overnight moorage, especially if you have a solar panel and don't have to use shore power. A 25' boat without shore power will save $10/night in most marinas in the Salish Sea compared to a 30' boat with shore power, and that adds up quickly if you are using docks 2-4 times per week. I also think that a 25' boat is the sweet spot between simplicity, easy single handing and docking in rough conditions, and being safe (perhaps not comfortable) in adverse conditions.
With the right outboard (25" prop shaft) a 25' boat won't swamp or caviatate the outboard frequently, even in 3' and 4' waves.
boats that I sail on regularly: Pearson 28-2, Rondar 505, Yankee 30, Blanchard Junior