I don't want to race, I'm not looking to cross oceans - I just want to get out of the city and onto the water with my dog and my wife and a picnic cooler and maybe spend the night outside with a beer in my hand.
You can do this very comfortably on a 25' boat. You can find nice examples for well under $10k and have a lot left in the budget. You'll want that anyway to cover unexpected maintenance (the first year with any new boat is expensive) and upgrades.
I cruised for 12 days on my Catalina 25 last summer and had a great time. The trip did get me thinking about an upgrade, but what really pushed the upgrade is a once a decade option (for me) to spend most of the summer sailing. My trip report from sailing the Catalina 25 is here:
Alex Wetmore is always busy with something… » Blog Archive » Sailing to the San Juans
Having owned a 25'/outboard boat and now owning a 29'/inboard boat I can say that the smaller boat is quite a bit cheaper and easier to maintain. Everything is simpler. It took me to the same destinations. Keep it simple.
Boat availability and what works well is quite different from the Chesapeake and Puget Sound, so I won't make specific boat suggestions. The Catalina 25 with a tall mast is an inexpensive option that worked well for me.
There are 27' boats that would be a good compromise between simplicity and space. Popular examples out here would be the Catalina 27, Cal 2-27, Pearson Triton, Albin Vega, Islander 28.