The project I'm on used TypeMock for many months. We actually just finished completely phasing it out in favor of Moq (completely free Apache 2.0 licensed mocking framework). You should definitely check out Moq if you haven't seen it. In addition to having the most intuitive syntax of any mocking tool I've seen, you get the benefits of compile time type checking. Very nice.
TypeMock has one significant benefit over Moq as I see it. Namely, it can mock anything. This includes sealed classes, non virtual methods, concrete types and pretty much anything else you can throw at it. If you're doing ASP.Net, and depending on how your code is structured, it can actually make mocking ASP.Net code behind classes a possibility. Quite neat.
However - We found that if you structure your code well, the benefits of TypeMock do not outweigh the price. Further, if you can't mock something with Moq, it probably means there's a smell there. TypeMock lets you be lazy, and I think that the code can suffer as a consequence. Moq and other mocking frameworks like it (RhinoMocks comes to mind) do make you think about your code as you're writing it, especially in terms of testability, but I would argue that's a good thing :) Further, our team ran in to several headaches trying to deploy TypeMock to our continuous integration server.
Long story short, TypeMock is a very powerful tool. As you mention, for unit testing old legacy code there aren't many better products. However, 1000 bucks gets you one TypeMock license, OR, a couple of resharper licenses, almost ten TD.Net licenses, a new continuous integration server or many other things. My own experience suggests that it's not worth it, but your mileage may vary!