"All of the prospective planning things seem to be in a far better shape than pre-Katrina," he added. "But I'm not so sure about the levees. ... We could conceivably be on the verge of a real-life testing of the stability of the levee repairs."
For Klaus Jacob, a special research scientist at the Lamont-Doherty Earth Observatory at Columbia University, it's more complicated.
"You have to realize the levees were built in the late '30s, and over the decades they evolved," Jacob said.
Year after year, land in the extreme Mississippi Delta, where New Orleans sits, sinks, said Jacob. Combine that with rising sea levels caused by global warming, and you've got a problem on your hands.
"The land sinks, and the levee sinks with the land; therefore they do not do as well a job as the engineers planned," he said.
Similarly, it's the levees that Sandy Rosenthal gets passionate about. A lifelong New Orleans resident-turned-activist, she lives uptown.
Speaking with a slight but unmistakable N'awlins accent, Rosenthal said, "If you would have asked me the day before Katrina [if I trusted those levees], I would have told you absolutely. They're built by the U.S. Army Corps of Engineers. Now even with the assurance that the levees are stronger than they were, I myself have little faith in those levees."
Like his fellow residents, Derrick Rogers, a 28-year-old sales manager who lives in the Broadmoor neighborhood and is working on his MBA at Tulane University, has already made reservations at hotels in Atlanta and Charlotte, N.C.
But Rogers seems less concerned about the potential physical devastation that Gustav might wreak; instead, he's concerned about killing the spirit of his hometown, a culturally rich place that's just beginning to refind its footing.
Rogers returned to his hometown after Katrina to take part in rebuilding the city. The momentum and energy, along with residents and tourism dollars, could be lost, he fears.
"I honestly feel that if the city floods like it did before, then that's pretty much it for New Orleans," he said.
ABC News' Scott Mayerowitz contributed to this report.