Similar interests, a little larger price range...
I think you and I pretty much agree that the Countryman S would be just about perfect. I myself would lean more towards the Nissan Juke SV in a direct comparison, but knowing that I've seen neither, it isn't a reasonable call to make.
I feel like the Honda Accord Coupe is a reasonable choice, but I'd only want to grab one in EV-V6 6MT form, and as I understand it, those are pretty hard to come by. Fortunately or unfortunately, there really aren't any direct competitors to it. The Altima Coupe is okay, but I feel like without a V6, they're fairly pointless... And at that price, you may as well be getting a 370Z. The only other "coupe" I can think of in that segment that is worth a look is the Passat CC, but that may be a bit too big for what you want. Still, a CC with the 2.0T and DSG would be a helluva lot of fun.
The American Contingent
I'd probably be willing to wait for a Ford Focus Titanium Sport early next year. Leather, MyTouch, other gizmos, plus a slightly detuned suspension/tire option from the ST. I understand it won't command a large price over the Titanium as it is, and you should be able to get it with the Dual-Clutch gearbox as well. As far as the bigger cars go, you could save your pennies for a Taurus SHO, but that is on the extreme high end of your budget. Leftover '10 models could go for cheap, assuming that there are any to begin with.
Over at GM, your choices narrow further. Knowing how you and I think about cars, we're still a ways out before the cooler cars are here. That being said, the Buick Regal is actually quite the car, and is a bit cheaper than what I thought it would be. I'd probably look into the CXL Turbo myself, although waiting for the GS Turbo (essentially the same thing as the Vauxhall Insignia VXR/Opel Astra OPC) would be a best-bet. What I like most about it is that it doesn't stand out too much, has the capability of doing great things, but is a comfortable sedan otherwise. James May loved the damn thing. That has to mean something.
At Chrysler? Meh. Just wait for the Fiats and Alfa Romeos to show up. The 500 is supposed to be awesome, and Dodge is supposed to carry some version of the Guietta for 2012.