Technologies that Have Exceeded Their Expectations?
I disagree about the CLI. When I sit down at a decade-old SGI or even a 5-year old RS/6000 running AIX, I find the CLI so primitive as to be almost useless. The GNU readline characters don't work for command editing, the history is almost unusable, there is no tab completion of binaries, filenames, or hostnames. ls is not in color, tar can't gunzip or bunzip2 (it requires a separate step), and tools like head and tail are missing command line options that I find invaluable.
And this is just the simple stuff. Since most of the afforementioned machines probably have tcsh as their best shell, doing something like a for loop on the command line is impossible. Don't even get me started about the pain of using an old version of Perl, "real" vi (rather than vim), or the very limited regular expressions of standard grep.
IMO comparing the CLI from a decade or more ago is like comparing the GUIs of then to those of now. Sure, Windows 1.0, a Mac circa 1985, or even a Lisa had a mouse, overlapping windows, and scrollbars. But it was crude and primitive compared to the powerful and polished GUI elements of KDE, Mac OS X, or even modern Windows. The CLI is just the same - it looks about the same to the untrained eye, but if you sit down and try to actually use it you'll see how far we have come.