First off, any dealer trying to charge a premium on a motorcycle in this economy is idiotic. My dealer sold me a brand new DR-Z at cost (they made money on the accessories I bought for it). This is because Suzuki is financially hosed at the moment. They didn’t even introduce 2010 models to the US because not nearly enough 2009 models sold. They’d be out of their minds to charge a premium (they might try, but they’ll probably still say yes to a low offer). Second, there were a surplus of used, low-mileage DR-Zs in my area starting around $4K, most with heavy modification (in a good way).
More expensive than a 250? Yes. Substantially so? Nope.