I think that's true, but I also think that these "technology-related things" are things that do not exist. Take your example: Windows has not improved in any way that is relevant to lawyers since Windows 2000. What is the point of upgrading?
I see many things in my practice where I could see technology making things more efficient. But almost never do I see legal technology that actually addresses that need. For example, the entire legal world runs on PDFs. Court opinions are in PDF form, documents are produced as PDFs, case filings are in PDFs, signed contracts are circulated as PDFs. But for some reason everyone wants to build web-based tools that cannot deal natively with PDFs, or by some miracle manages to be worse than Acrobat at handling them.
In another example, client confidentiality is a big deal in law firms. But everyone wants to build web-based tools that upload unencrypted documents god-only-knows where.
In a final example: web technology is built on getting good answers to questions everyone is asking. That's the premise underlying Google: if a website is popular as a link target, it's probably a good result. Law is often about exactly the opposite: how do I distinguish my case from all the other ones that go in a way that's bad for my client? In other words, what are the parameters that create the exception to the rule? The techniques used everywhere else on the web are awful for that.