A family member is a lawyer in the Worker's Comp, SS, and Family Law space. THE software for lawyers in this space is called A1 Law. It solves a lot of real problems lawyers in that space have (form letter generation, calendar integration, case management)... but it's so slow to use new technologies. They advertise PalmOS integration. My family member has to have their own server in a closet running the server versio…
A lawyer friend of mine told me his firm doesn't use software to check all the "hereafter referred to" are bound to their template and vice-versa. They instead have to print the document and go through it with a highlighter. The firm charges their clients on an hourly basis, so they don't really have an incentive to be more efficient.
Logojoy, for instance, is an example of a service that supplants human labor with a single "good-enough" deliverable at a low price, and does so in a fraction of the amount of time. I imagine this would be much more difficult in legal settings, but LegalZoom seems to be alive and kicking, so it must be possible.