Re: Sailboat under $5000 for Puget Sound
He is in Port Townsend. I'd suggest going south to Port Ludlow or Port Gamble, both are very close and have good anchoring conditions. You can save some time by motoring through the canal at the south end of Port Townsend Bay.
What is your anchor rode?
Anchoring is fun and you can just go out for a day sail and practice at lunch time too.
There is a big swap meet at Fisheries Supply in Seattle on April 13th. You have to get there extremely early (the sale starts around 5am and is all but done by 10am), but there are usually a number of dinghies and they are usually quite a bit cheaper than what I see them listed for on Craigslist. It also gives you a chance to check out many dinghies at once. Given normal nightly moorage rates around here a used dinghy will pay for itself fairly quickly.
I'd also recommend walking around the big marina at Port Townsend and looking at dinghy racks (if they have them installed per slip). In Shilshole (Seattle) it's easy to tell who might have dinghies for sale, they normally have them piled up on their dinghy rack. Since you'll likely be towing (and rowing) it all of the time I'd recommend looking for a small rigid one. They tow better than inflatables (with the major downside that they can swamp more easily) and row much better than an inflatable.
1986 Pearson 28-2 "Elena"