4. Ask, and You Shall Receive.

In light of the economic crunch, some vendors are coming up with creative financing to entice would-be customers to sign deals, says Schleiden. If they don't, you should. "We have a list of side perks we typically ask the vendor for," says Schleiden. These include cost caps on future maintenance and licensing increases, and free first-year maintenance. "We've never been successful in getting them all, but we typically get several," he says.

Never hesitate to ask vendors for concessions, says Gartner Inc. analyst . During the course of contract negotiations, software vendors will typically go through a discounting process "that leads the customer to believe that [the salespeople] won't be able to feed their own children tomorrow because they gave them such a great deal," she says.

But don't worry about the vendors. They "always tend to hold back money," Disbrow says. Your goal should be to not leave any of that money on the table.

5. Eliminate Phantom Systems.