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There's Applescript support, so you could probably cobble together a script that'd launch your multiple windows & commands.

There's also Window->Save Window Arrangement, but I believe that only allows for a single arrangement.

Feel free to add a feature request at http://code.google.com/p/iterm2/issues/list (There's plans for eventually moving everything over to github, but the issues will get migrated too)

I'm working on improving the preferences UI and back-end, but I'm learning obj-c and Cocoa as I go, so it's a slowish process :)



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