font naming

I have long used Torino BT as a text font, and recently obtained Torino OPTI Bold, Extra Bold, Heavy. I was delighted to finally have a bold, but Torino doesn't co-operate. It 'substitutes' a font like Old Standard bold, which is similar, but will not show Torino OPTI Bold, now named as simply, 'Torino bold' Having re-named the entire family, the problem persists. I'm stumped. Can anyone shed light?

One of the titles I'm considering is already taken by a free font. Is this legal (since the original isn't commercial)?

But here's a better example:
2010 (free):
2011 (commercial):

I've been working on a new font that for the time being is called New Cuisine. When I go to test things in Illustrator the menu ignores the New and places it where Cuisine would fall. Is the word New a trigger in Adobe apps making it use Cuisine as the family name even though its a single font for now?

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