You forgot the nettles! You know, the little sob's that sting you everytime you jump in the water to cool off.
Seriously, a boat makes a great second home and the loan interest is tax-deductible!
When I couldn't find a piece of property I could afford on Lake George, NY, my wife convinced me to buy a boat. We lived on that boat every weekend, from May-October, and had a fantastic time. It was also nice knowing that for $18K, we got to swim and play in the same water that the rich folks did. It was the release valve needed for all the stress we accumulated during the week. I'm still boating 22 years later.
As far as the Chesapeake goes, it's a great cruising ground. I think of it as a Thomas' english muffin, with all sorts of nooks and crannies to explore. Practice your anchoring skills and the Bay will become your personal playground.
As far as boat choices go, sail if you plan on taking long cruises, sail or power if you don't.
Sail pros-Less expensiive to purchase and maintain, use less fuel, peace and quiet, hold their value, and you'll get immediate acceptance into the sailing community.
Sail cons- Deeper draft, longer operational learning curve, more work involved, and slow speed.
Power pros- Fairly shallow draft (for example my 35' Mainship only drew 3.5 ft.), can get you where you want to go quickly, easier to operate, shorter learning curve, and usually offers more creature comforts.
Power cons- More expensive to operate and maintain, high noise level when operating, bigger depreciation, and sailboaters will generally hate you.
Whatever you decide, a boat makes a great second home and if both of you enjoy "camping on the water" you'll never regret your decision.