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Syntax specific settings don't work either, they're just ignored - this used to work but stopped a few beta releases ago (I'm on 2180 now).

AFAIK, the menu toggle is tab specific. So when opening a new file, it should take the setting from the settings files, right? It doesn't. For me, it's always no wrapping, no matter what's specified in the syntax specific settings or what's been clicked on in the menu before.
You're completely right.

Still, Sublime Text doesn't do this. You can only column select by dragging your mouse, not by moving your cursor by clicking (with shift).

Sorry to bring this down to a pure feature comparison, but TextMate is a lot more flexible here, handling softwrapped lines more consistently, given quite good support in modifying your selection via mouse/keyboard and switching between column/normal selection mode. Just take it as an example of how that feature could work.
I've switched to Sublime completely, except for this. Whenever I just want to quickly sketch some ruby code and see how something reacts, I have to start TextMate. I already tried to build a build system that acts like that myself, but AFAIK the build system only receives the filename when invoked, which is empty for an unsaved file. Receiving/being able to access the file content would be great.
Actually, this is the standard behaviour: Place your cursor somewhere, scroll somewhere else, click with shift pressed - this creates the same selection as if you selected by dragging. So alt-clicking would be the same: place your cursor somewhere, scroll somewhere else, click with alt pressed - same selection than dragging while having alt pressed.
So, -n is just used for files and will be ignored for directories. That's what I meant talking of inconsistency: The default for files is to open in the current window which you can override with -n whereas the default for directories is to open in a new window which you can override with -a.

I didn't expect sublime to behave differently depending on whether I specify a file or a directory. I'd rather prefer the same behavior for both and just one switch to override that behavior, but If this is not the intention, then ok.
Just downloaded the 2144, and things improved:

`subl -n a_directory` doesn't open another empty sublime window


`subl a_directory` still opens a new sublime window instead of adding the directory to the current sublime window

This might be intended behavior, but it seems inconsistent, since `subl a_directory` and `subl -n a_directory` don't behave any different.