Check out appomatox river company in the fall.... I've had good luck buying boats from them in their farmville store. They once sold me a brand new $2,000 MSRP tandem for $1200 in the fall. I ended up selling that boat on, but it was a great price for a serious tandem. They do sell used boats and demo boats as well.
I completely get why you'd be frustrated in a sit on top, but at least you're on the water. Watch your craigslist, norfolk's craigslist and charlottesville's craigslist.... Things sell cheaper on richmond's craigslist than DC's. When I was living in Richmond, I bought a 14 foot perception catalina off charlottesville's craigslist for $300.... Was it the boat that I ultimately wanted? No, but it was $300 and good enough to paddle around in & have fun, relatively lightweight. When I got to the point that I was going to be touring, doing open water crossings, dealing with waves, and needed a faster boat to keep up with the person I was paddling with, etc., I found a better boat at a good price, the catalina got sold for $300 & I bought the next boat.
I still don't have the boat I ultimately want - but I've got one that I love in certain conditions and absolutely curse in other conditions. But it does what I want it to do... now if it was a foot or so longer, I'd be thrilled :) And if I buy a new boat or the bf ever finishes the boat he's building me, I'm still keeping my avatar around. I can already tell looking at the shape of the boat the bf's building that I'm really going to hate it in certain conditions - but I'm going to be able to fill it up with a ton of gear.

