Freecell Solver (one of my projects) is such a case. Its --help screen now takes seven clicks to display entirely when invoked with "fc-solve -h | less". The problem is that people like choices, but don't want to be confused with a lot of options. If the program does nothing (or misbehaves in the first board layout you try) and you want a quick answer, you're not going to read through seven pages. Spolsky tends to be a bit GUIish, but the same rule applies to commandline programs.
Several solutions have been brought forth to deal with this situation:
Here is my take on the pros and cons of each approach:
The CVS one is a bit annoying because I instinctively type "cvs --help" and get something absolutely useless. (This could be solved with a shell function, though).
-h and --help distinguishing is ok, but you may eventually make --help unusable, too.
The RTFM option: Many users will not bother to read a different source, so you may be losing some of them there. Also, if the man page is bloated, you are back to square one.
The Perl solution is not bad as long as you make sure the relevant parts of the man page are not bloated, and outsource things to different man pages. Website META Language has an interactive application for displaying and accessing its various man pages.
My problem with Freecell Solver is that I want it be portable to Win32 and other non-Unix platforms. If you stick to Unix, you can stay with the Perl approach and simply make sure your man pages are sane (and that you have HTML documentation and, optionally, a PDF file).
In any case, my portable solution is a combination of the CVS and Perl solutions. I am going to have a default CVS-like help screen, which could later be changed to something else, using an environment variable.
Here's what I'm going to write:
fc-solve [flags] [board_file|-] Reads board from standard input by default or if a "-" is specified. - If it takes too long to finish, try one of the commandline configurations presented in --help-configs. - If it erroneously reports a board as unsolvable, try "-to 01ABCDE". - If the solution is too long, try running it with the "-opt" flag or with "--method a-star". - If you want to present the moves only, try "-m" (long notation) or "-m -sn" (very compact). - For a description of all the options, type "--help-all". - For other problems, type "fc-solve --help-problems". - To turn --help back into something more useful, read "--help-real-help". Contact Shlomi Fish, email@example.com for more information.
This deals with common problems in a graceful way (of course, I'll have to implement the other help screens). If you're asking why I don't configure Freecell Solver so it won't have these problems, you're asking a good question. However, the default configuration works well for most of the boards out there, and I don't want to give the user something more complex that may or may not work better (and is itself a compound configuration).
I will use an environment variable named FREECELL_SOLVER_DEFAULT_HELP (I'm a bit obsessed with maintaining namespace integrity) to specify the default help screen. That way, the user can modify the help screen to something more useful than the summary (which would always be available in --help-summary). I haven't used environment variables before, but I don't think I have a choice now.
I guess I'll have to do something regarding usability before I add support for system threads. That's why I'm planning that the 2.7.x tree will be dedicated entirely to rethinking usability. The factoring of the help screens would be one thing, but I'll also try to have better documentation with more diverse formats than text files (God bless Perl POD and DocBook), and other such changes.
If you think human factors engineering does not apply to commandline programs, think again. Even in the Unix world, where Real Men(tm) and Real Women(tm) use commandline utilities like it was their second nature, you still need to make sure your program behaves in a sensible way. When was the last time you managed to find a forgotten flag in the gcc man page in less than two minutes?
 Freecell Solver is thread-safe and can task switch but cannot be thread-enabled. If you are asking why I need to make it thread-enabled when most Freecell users will never need to run it on an SMP machine, my answer is: Just for fun(tm).