The problem is that directory creation code for pages does not update them in --server --auto mode when user modifies the source file. It generates them just during initial generation after launching jekyll.
I introduced pretty_flat mode which behaves consistently in my opinion. It does not create directories /pagename/index.html for pages but generates simple /pagename and works consistently both in batch and --server --auto mode. My other pull requests are solving the problem of mime type with naked /pagename urls (which was probably your original motivation why to implement it as /pagename/index.html)
introducing pretty_flat permalink mode
it behaves like pretty mode, but it does not create directories for non-index pages. it also works correctly in --server --auto mode.
I like this idea, but this implementation only works for pages. To merge this in, it will need to work for posts as well.
Agreed, this should be more general. @darwin, want me to take a stab at it or do you have a solution in mind?
@parkr yes, that would be great. Thanks!
@darwin How would you envision :pretty_flat for posts? "/:categories/:year/:month/:day/:title" or "/:categories-:year-:month-:day-:title"?
@parkr I'm sorry I have unloaded it from my head. I have no idea how this should work for posts.
@darwin Ok, I'm going to use the latter.
@mojombo Any thoughts on these PRs?
We seem to have lost interest in this feature. Closing.