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): http://www.dafont.com/nouvelle-vague.font
2011 (commercial): http://www.myfonts.com/fonts/anatoletype/nouvelle-vague/

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?