When interviewing, try to engage in scenario brainstorming or role playing, not definition swapping. In this case try to engage an applicant in telling their story about what they would expect "...when taking over responsibility for the main finance system, which this department and that group use daily for these things, and there are a couple things that are wrong with it today, and oh by the way, there is a upgrade release scheduled for three months from now that will allow direct integration with this new banking partner for 1099 processing". Make the scenario specific and real for your situation, and get them talking.
The important thing is to draw out from them not only what they would do, but almost as importantly, what they know to expect. If your candidate sits across from you and weaves a story about getting up to speed in a couple days and making major changes up through production by next Friday, without asking any of the important questions and impressing you with their effectiveness, doubt their experience (and if you are in a regulated industry or, unfortunately, Big Company, possibly their sanity). If instead they ask good questions about what the environment is like today, what's the review process, who makes the decisions about functionality, is there a testing environment, is the code testable or are there unit tests (gasp) in place, and what happens today if a change needs to get in place by Friday - hey, they've probably been here and done this before.
You of course want to hear how they would make sure existing functionality works and time bombs aren't being set but you also want to hear them making reference to things they would be doing so that this project becomes better, easier to work with, and more fun over time. The activities they specifically are engaging in to turn the inherited legacy project into a rocking world of fun should come through in their storytelling. I mean, they are planning on doing that, right?
Great interviews are conversations and experience sharing and story telling. Draw those stories out, bounce them against the b.s. shield, and go.