Technical Debt

Martin Fowler wrote a post about technical debt that struck a nerve we me and others.

Our company as well as others I've worked for in the past and I suspect everyone else struggles with this every day. How does one help the business side of the house understand the implications of the quick fix? I don't know that this is a solvable problem because it requires predicting the future. Applying a quick fix to application A is the right solution if it so happens that it is retired before the accumulated debt becomes overwhelming.

So how do we measure technical debt? If we could the argument for time to rewrite vs. fix would be easy.