Not sure why people are having so much difficulty with this, but I've done it routinely. In the latest version of MAME, the screen rotation options are set in the [romname].cfg file in the CFG folder (by default). If your .INI file for a game is set up correctly to display multiple screens and assign specific views from the .LAY file to each screen, the rotation for each can be set using the regular MAME config menu (with game running, Tab Key > Video Options > Screen # > Rotation). This should save the screen rotation to the game's .CFG file.
That said, I don't know how you would do it as a default for ALL games, but for that to work, every artwork .LAY file would have to have the same set of view names--not practical.
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I have officially retired from sucking at everything I do. Life is much easier now.
My MAME/MESS artwork files: https://drive.google.com/open?id=1ABxeKgNIrKlIsyck7dx4V241NFQDWAF4
Related screen shots: https://drive.google.com/open?id=1U5IbvbVzYW97PuOOQuocvZFE_YJz7WIn
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Re: Running Duel Monitors with Different orientations
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