I followed most of the links from there, including that one and found a lot of interesting stuff. I think that some people have taken the money analogy a little too far, and many of them miss one quietly stated but very important point from Martin Fowler's blog entry:

The tricky thing about technical debt, of course, is that unlike money it's impossible to measure effectively.

Another analogy that sprang to my mind is that balancing technical debt on legacy code is a lot like running an old car. There comes a point where it no longer makes sense to properly maintain that old banger with new parts, at which point patching it up and 'making do', till you saved enough to fund a replacement can make sound economics.

There is also another floating around in my brain about not shelling out for a infra-red grill, convection and microwave combo-oven, if all you are ever going to do with it is defrost a few steaks and zap some left overs--but then I remember the behemoth that sits in my kitchen gathering dust, getting use one or twice a week :)