My wife's car is a 2009 Eos - same 2.0T and DSG tranny. Her car was effected by the DSG recall - they needed to replace a transmission fluid temp sensor. With that fix, the transmision has been fine for 6 months now. The motor is quite a gem -- IIRC, it is the successor to the 1.8T which, IMHO, was a decent motor as well. Za Turbo ist gut!
I wouldn't worry too much about the DSG transmission 'issues.' It is one of the slickest manu-matics out there.
As for the asking price -- go in and low-ball the dealer. Tell him you'll buy it for $15,000 plus tags, tax, and fees. He'll probably laugh, but eventuall come down a little. Given the current auto market climate, you should be able to get that car for under $17k (plus tags, tax, and fees). Note- just because certain documentation fees are on the sales order, that doesn't mean that price isn't negotiable either -- you should be able to get them to drop the 'documentation fee' by at least 50%.
Don't fall in love with the car, and don't show the dealer that you really want the car. Be willing to walk away. Don't listen to his "at $17,981, we're not making any profit on this car..." Trust me - they are making plenty of profit. And they deserve to make some money, but a. not that much, and b. not from your sale.
Even though it is at a dealership, you could still take the car for a Pre-purchase inspection at another place. If the previous owner was a younger driver, chances are that GTI was ridden hard, and put away wet. A PPI should be able to help you determine what condition that car's really in.
If you need to finance the car, you don't necessarily have to finance through the dealership or VW. Check with your own bank, and see if their rates are better. Also - if you have a checking/saving account and opt for the direct withdrawl to make payments, that can drop your interest rate by a little as well.
Good luck!
-Z-man.