Re: Sailboat under $5000 for Puget Sound
WItha smaller boat, inexperience, I would go to Hadlock of ludlow frankly. Ludlow would be better than the 20+ south to Port madison! Ludlow has good anchoring, protected etc. probably a 3-6hr trip depending upon if sailing vs motoring, wind speed for sailing etc.
WM and a few others also have pure rowing inflatables for $2-400, that would probably be best for a smaller boat vs pulling/towing an 8' wood, or blown up motor style inflatable. get one of the bigger foot pumps, should have the boat blown up in less than 5 maybe 10 min. over the side, and in towards shore you go.
At ludlow, since you pay for your slip for the weekend, andit is reserved in yourname per say, you could use the slip, go out and practice anchoring, come back in and tie up, use the shore facilities, until you get a dinghy too.
I've alsonot had a lot of luck locally with danforths. a small plow style ifyou will, like the lewmar 5-7.5kg bruce knockoff with 10-20' of chain would allow me to sleep in your boat overnight better. As this style will reset better than a danforth of the tide changes etc. THere is a 9 lb fastset plow style at WM also. Not sure if PT has one is stock at the moment, but they get weekly replenishments, so you could get one at some point in time if wanting to work out of a local, walk to store vs driving into seattle etc.
She drives me boat,
I drives me dinghy!