Is there a SO family + SE site where I can ask questions related to fonts and also font recommendations?
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Take a look at http://ui.stackexchange.com/ - but search first and look for any existing questions.
In fact there's already a question that might fit the bill - http://ui.stackexchange.com/questions/114/what-fonts-are-good-and-which-ones-should-we-avoid-for-our-applications-ui
However, font recommendations can be subjective so be careful how you word your question (if you do decide to post) and try to make it as objective as possible.