In a recent post to his site Keith Casey mentions something that should be obvious to most software developers (and managers of developers out there) but is easy to forget - technical debt doesn't just disappear, even if the related resources change dramatically.

Just because you set a codebase aside and do it the "right" way, your problems don't disappear. The same bugs that annoyed people yesterday will be there today and tomorrow. In fact, when the bugs are still there a week, month, or year from now, they move beyond annoyances and into frustrations as people think (or say) things like "this has been broken for years.. why haven't they fixed it!?"

He notes that, while tossing the entire codebase out the window and starting over again (a move very, very rarely shown a good idea), you'll still end up with issues - this time involving resources and the work needed to sift through all of the bugs in the new code.