Re: Second boat suggestions?
hi Jimgo: its great that you've got your needs identified. Sorry it took the loss of your boat to define them.
I'm not sure how many of your boat needs will change if you change your sailing location.
Lets look at 'quality' boats under 10K, that could fit.
Sabre, Cape Dory, Alberg to name a few. Problem with them is their shoal draft version, isnt very shoal. I find the less I draw, the more chances I take, ergo touch bottom more often than I did when I had a big boat with more keel. My present boat draws 2'11" and I take advantage of that by sailing in places I've never been. Rivers and back bay sailing with the tide have opened up a new pallet on which to paint my daysails.
In looking at your price point, you'll be testing your skills to 'fix' things that will be wrong. While the boats I mentioned will have a big boat feel, they'll be older than catalina/o'day/hunter's.
As to where, which should be on the top of the list, then the boat type should follow. I'd pick Cape May or something near, on the Ocean or the Bay side of it. Mooring in Cape May harbor is a hoot. Lots of transients, lots of locals. A good blend of providers of local knowledge and possible future destinations. Cape May is a good jumping point to LIS, Block Island, Newport.
Caleb said it best 'its all about compromises'. There's no perfect boat and no perfect home port.